Substituted pyridine and pyrimidine, processes for their preparation and their use as pesticides

ABSTRACT

Compounds of formula I, N-oxides or salts, thereof in which q is 0, 1 or 2 A is CH and D is N+Rx1/n Qn- or A is N and D is N+Rx1/n Qn- or A is CH or N and D is N or A is N+Rx1/n Qn- and D is N, R is CR6R7DaR8, Qn- is an inorganic or organic anion, n being 1, 2, 3 or 4; X is NH, O or S(O)q, (q is 0, 1 or 2); and the R groups have various meanings as defined in the claims are useful pesticidal, especially insecticidal activity.

Substituted pyridine and pyrimidines, processes for their preparation and their use as pesticides

The invention relates to novel substituted pyridines and pyrimidines and condensed systems derived therefrom, processes for their preparation and their use as pesticides, especially insecticides and acaricides.

It is already known that certain 4-cycloalkylamino- and -alkoxy-heterocycles have fungicidal, acaricidal and insecticidal activity (for example DE 42 08 254)

However, the biological activity of these compounds, in particular at low application rates and concentrations, is not satisfactory in all use examples.

It has now been found that compounds of formula I have been found ##STR2## in which the radicals and groups are as defined below, which, while showing good tolerance by plants and favourable toxicity in respect of warm-blooded animals, are highly suitable as pesticides and especially for controlling insects and acarids. Some compounds also show fungicidal activity.

The invention therefore relates to compounds of the formula I, their N-oxides and salts in which

q is 0, 1 or 2

R¹ is hydrogen, halogen, (C₁ -C₈)-alkyl, (C₁ -C₈)-haloalkyl, (C₁ -C₈)-alkoxy or (C₃ -C₆)-cycloalkyl;

R² and R³ are identical or different and are each hydrogen, (C₁ -C₈)-alkyl, (C₂ -C₈)-alkenyl, (C₂ -C₈)-alkynyl, (C₁ -C₈)-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C₁ -C₈)-alkoxycarbonyl, (C₁ -C₈)-alkylthio, (C₁ -C₈)-alkylsulfinyl, (C₁ -C₈)-alkylsulfonyl, amino; (C₁ -C₈)-alkylamino, (C₁ -C₈)-dialkylamino or (C₃ -C₆)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl groups or the groups derived from them, such as alkoxy, alkynyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, a saturated carbon unit can be replaced by a hetero atom unit such as oxygen, S(O)_(x), where x=0, 1 or 2 or by dimethylsilyl and further in these groups or derived groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or

R² and R³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH₂, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, preferably trifluoromethyl, halogen, (C₁ -C₄)-alkoxy or (C₁ -C₄)-haloalkoxy; or

R² and R³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH₂ groups and which may be substituted by 1, 2 or 3 (C₁ -C₄)-alkyl groups;

A is CH and D is N⁺ R×1/n Q^(n-) or

A is N and D is N⁺ R×1/n Q^(n-) or

A is CH or N and D is N or

A is N⁺ R×1/n Q^(n-) and D is N,

R is CR⁶ R⁷ D^(a) R⁸,

Q^(n-) an inorganic or organic anion, n being 1, 2, 3 or 4;

X is NH, O or S(O)_(q), (q is 0, 1 or 2);

R⁴ and R^(4'), which may be the same or different, are hydrogen, halogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-halogenalkyl, (C₁ -C₄)-alkoxy or (C₁ -C₄)-alkylthio;

R⁵ is the group ##STR3## l is 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4,

each R⁹, which may be the same or different from any other R⁹, is (C₂ -C₈)-haloalkenyloxy, (C₂ -C₈)-haloalkynyl, (C₂ -C₈)-haloalkynyloxy, (C₁ -C₄)-haloalkoxy-(C₁ -C₄)-haloalkoxy, oxiran-2-ylmethoxy, oxetan-2-ylmethoxy, isopropylidenoamino-oxy, isopropylidenamino-oxy-(C₁ -C₄)-alkoxy, formyl, --SF₅, hydroxy or heterocyclyloxy, in which the last named group may be substituted by up to three (in the case of fluorine up to the maximum number), of the same or different D¹ R¹², cyano, nitro or halogen, or

R⁹ is a group Z--R¹¹, in which

Z is OSO₂, NR¹³ SO₂, UC(═W)V, U¹ P(W¹)(V¹ R¹¹)V², SO₂ NR¹³, SO₂ O, NR¹³ SO₂ NR¹³, OSO₂ NR¹³, NR¹³ SO₂ O, Si(OR)¹³ R¹³, N(O)R¹³, NR¹³ O, NR¹³ NR¹³, N═N, N═, NR¹³ --N═, D¹ --N═ and

U¹ is a direct bond, oxygen, NR¹³ or sulfur,

U is oxygen, NR¹³ or sulfur, or when W or V is NR¹³ or sulfur, it can also be a direct bond,

W is oxygen, NR¹³⁰ or sulfur, preferably oxygen, and

R¹³⁰ is hydrogen, nitro, cyano, optionally substituted alkyl, optionally substituted acyloxy, optionally substituted aryl, optionally substituted heteroaryl, hydroxy, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, mono- or disubstituiertes amino;

W¹ is oxygen or sulfur,

V, V¹, V², independently of each other are a direct bond, NR¹³, oxygen or sulfur,

each R¹³, which may be the same or different from any other R¹³, is hydroxy, alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituiertes amino, optionally substituted acyl or optionally substituted acyloxy,

R¹¹ is (C₁ -C₂₀)-alkyl, (C₂ -C₂₀)-alkenyl, (C₂ -C₂₀)-alkynyl, (C₃ -C₈)-cycloalky or (C₄ -C₈)-cycloalkenyl, in which groups optionally one or more, generally up to three, CH₂ -groups can be replaced by carbonyl-, thiocarbonyl or heteroatom units, preferably O, S, SO, SO₂, NR¹³ or SiR¹⁶ R¹⁷, and these groups may be substituted by up to three (in the case of fluorine up to the maximum number), of the same or different D² R¹⁴, cyano, nitro or halogen, or

R¹¹ is hydrogen, aryl or heterocyclyl, in which the last named group may be substituted by up to three (in the case of fluorine up to the maximum number), of the same or different D³ R¹⁵, cyano, nitro or halogen, or when V is NR¹³, R¹³ and R¹¹ can together form a 4- to 8-membered ring, in which one or two CH₂ -groups, preferably one CH₂ -group is replaced by a hetero atom unit, preferably oxygen, S(O)_(t), (where=0, 1 or 2), or NR¹⁹, in which

D¹, D² and D³, independently of each other, are a direct bond, oxygen, S(O)_(k), SO₂ O, OSO₂, CO, OCO, COO, NR^(13'), SO₂ --NR^(13'), NR^(13') SO₂, ONR^(13'), NR^(13') O, NR^(13') CO, CONR^(13') or SiR¹⁶ R¹⁷, and k=0, 1 or 2 and R^(13') has the same meaning as R¹³,

R¹⁶, R¹⁷, independently of each other, are (C₁ -C₄)-alkyl;

R¹², R¹⁴ and R¹⁵ are hydrogen, C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl, C₂ -C₈ -alkynyl, C₃ -C₈ -cycloalkyl, C₄ -C₈ -cycloalkenyl, C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl, C₄ -C₈ -cycloalkenyl-C₁ -C₄ -alkyl, aryl, heterocyclyl, aryl-C₁ -C₄ -alkyl or heterocyclyl-C₁ -C₄ -alkyl bedeutet, in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, preferably up to three, CH₂ -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more, preferably up to three, (in the case of halogen up to the maximum number), of the same or different groups selected from halogen, hydroxy and cyano and in the case of of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more, preferably up to three, (in the case of halogen up to the maximum number), of the same or different substituents R¹⁸ ;

R¹⁸ is (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-haloalkoxy, cyano, nitro or halogen;

R¹⁹ is hydrogen, (C₁ -C₈)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkythio, (C₃ -C₅)-cycloalkyl, (C₂ -C₄)-alkenyl, (C₂ -C₄)-alkynyl, (C₁ -C₄)-alkanoyl, (C₂ -C₄)-haloalkanoyl, (C₂ -C₄)-alkoxyalkyl, phenyl-(C₁ -C₄)-alkyl or phenyl and the phenyl groups are unsubstituted or substituted by one or more, preferably up to three, (in the case of fluorine up to the maximum number), of the same or different substituents R²⁰,

R²⁰ is (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylthio, halogen or cyano;

R¹⁰ is cyano, nitro, halogen, C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl, C₂ -C₈ -alkynyl, C₃ -C₈ -cycloalkyl, C₄ -C₈ -cycloalkenyl, C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl, C₄ -C₈ -cycloalkenyl-C₁ -C₄ -alkyl, aryl, heterocyclyl, aryl-C₁ -C₄ -alkyl or heterocyclyl-C₁ -C₄ -alkyl in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, preferably up to three, CH₂ -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more, preferably up to three, (in the case of halogen up to the maximum number), of the same or different groups selected from halogen, hydroxy and cyano and in the case of of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more, preferably up to three, (in the case of halogen up to the maximum number), of the same or different substituents R²¹,

R²¹ has the same meaning as R¹⁸, or

two adjacent R⁹ and/or R¹⁰ groups together with the carbon atoms two which they are attached can form an unsaturated 5- or 6-membered carbocyclic ring, which in a 5 membered ring, a CH₂ can be replaced by an oxygen- or sulfur atom and in a 6 membered ring, one or two CH units can be replaced by one or two nitrogen atoms or substituted by 1, 2 or 3 of the same or different groups selected from (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (preferably trifluormethyl), halogen, (C₁ -C₄)-alkoxy or (C₁ -C₄)-haloalkoxy; or

two adjacent R⁹ and/or R¹⁰ groups together with the carbon atoms to which they are attached can form a saturated 5- or 6- or 7 membered carbocyclic ring, in which, one or two CH₂ units can be replaced by one or two oxygen and/or sulfur and can be substituted by 1, 2 or 3 (C₁ -C₄)-alkyl groups, and further when

A is CH and D is N⁺ R×1/n Q^(n-) or

A is N and D is N⁺ R×1/n Q or

A is N⁺ R×1/n Q^(n-) and D is N

R⁹ can also be (C₂ -C₆)-alkynyl, (C₂ -C₆)-alkynyloxy or (C₂ -C₆)-haloalkenyl;

R⁶ is hydrogen, halogen or C₁ -C₄ -alkyl or a negative charge, which can represent Q^(n-)

R⁷ is hydrogen, halogen, CN, nitro, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₄)-alkylcarbamoyl, di-(C₁ -C₄)-alkylcarbamoyl, (C₁ -C₈)-alkoxy, (C₁ -C₈)-alkyl, (C₂ -C₈)-alkenyl, (C₂ -C₈)-alkynyl, aryl or (C₃ -C₈)-cycloalkyl.

D^(a) is a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SO₂, C(═W^(a)), OC(═W^(a)), U^(a) (C═W^(a))V^(a) (U^(a) and V^(a) are a direct bond, NR⁷⁰, S or O, except V^(a) is not a bond when U^(a) is bond or O), SiR⁷² R⁷³, U^(b) (P═W^(b))V^(b) V^(c), U^(b) (SO₂)U^(c) (one of U^(b) and U^(c) is a direct bond, NR⁷⁰, S or O and the other is NR⁷⁰), U^(a) (CW^(a))(CW^(a))V^(b), NR⁷⁰ O, O NR⁷⁰, NR⁷⁰ NR⁷⁰, N═N, --N═, --NR⁷⁰ --N═ --O--N═, and

W^(a) is O, S or NR⁷¹ ;

W^(b) is O or S;

U^(a), V^(b) and V^(c), independently of each other are a direct bond, NR⁷⁰, S or O each R⁷⁰, which may be the same or different from any other R⁷⁰, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R⁶, R¹¹² OR R¹¹³, respectively with the D^(a), D¹² OR. D¹³ to which they are attached.

each R⁷¹, which may be the same or different from any other R⁷¹, is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy;

R⁷² and R⁷³ are alkyl or optionally substituted aryl; and

R⁸ is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH₂ units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO₂, NR⁷⁰ or Si R⁷² R⁷³ and can also be substituted by nitro, halogen, SF₅ or D¹² R¹¹², and in the case D^(a) is U^(b) P(═W^(b))V^(b) V^(c), the two R⁶ groups together with the V^(b) PV^(c), to which they are attached can form a 4 to 8 membered ring, D¹² is a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SiR⁷² R⁷³, U'(CW')V', U^(1') (PW^(1'))V^(1') V^(2'), U^(2') (SO₂)U^(3'), Si(OR⁷²)R⁷³, Si(OR⁷²)(OR⁷³), NR⁷⁰ O, ONR⁷⁰, NR⁷⁰ NR⁷⁰, N═N, ═N--, ═N--NR70-- ═N--O--, --N═, --NR⁷⁰ --N═ or --O--N═ and

U', U^(1'), V', V^(1') and V^(2'), independently of each other are a direct bond, NR⁷⁰, S or O

W' is O, S or NR⁷¹ ;

W^(1') is or S;

U^(2') and U^(3'), independently of each other are a direct bond, NR⁷⁰ or O;

R¹¹² is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH₂ units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO₂, NR⁷⁰ or SiR⁷² R⁷³ and can also be substituted by nitro, halogen, SF₅ or D¹³ R¹¹³ and in which two adjacent D¹² R¹¹² together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C₁ -C₄ -alkyl; is a negative charge for D¹² ═(CO)O, (SO₂)O, U^(1') (PW^(1'))V^(1') O which replaces the ion Q^(n-) ; or

R¹¹² is hydrogen when D¹² is O(CO)NH, NR⁷⁰ (CO)NH, O(CS)NH, NR⁷⁰ (CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰ (CO), SO2NH;

D¹³ has the same meaning as D¹² and R¹¹³ has the same meaning as R¹¹².

Aryl is usually a naphthyl or phenyl group, optionally substituted by one or more, preferably up to five, in particular up to three, identical or different radicals selected from the group consisting of

halogen,

(C₃ -C₈)-cycloalkyl,

(C₃ -C₈)-cycloalkenyl,

phenoxy,

substituted phenoxy,

phenylthio,

substituted phenylthio,

phenyl,

substituted phenyl,

optionally substituted heterocyclyl,

optionally substituted heterocyclyloxy,

optionally substituted heterocyclylthio

NO₂,

--C(O)--R¹³³,

acetoxy,

hydroxyl,

cyano,

SiR¹⁴⁴ R¹⁵⁵ R¹⁶⁶,

O--SiR¹⁴⁴ R¹⁵⁵ R¹⁶⁶,

NR¹⁷⁷ R¹⁸⁸

S(O)R¹⁹⁹,

SO₂ R¹⁹⁹,

(C₁ -C₁₂)-alkyl,

(C₂ -C₁₂)-alkenyl,

(C₁ -C₁₂)-alkoxy and

(C₁ -C₁₂)-alkylthio; and

R¹³³ is (C₁ -C₇)-alkyl, halo-(C₁ -C₇)-alkyl, (C₃ -C₇)-cycloalkyl, halo-(C-C₇)-cycloalkyl, (C₁ -C₇)-alkoxy, phenyl or substituted phenyl;

R¹⁴⁴, R¹⁵⁵ and R¹⁶⁶ are identical or different and are each independently of one another (C₁ -C₄)-alkyl, phenyl and/or substituted phenyl;

R¹⁷⁷ and R¹⁸⁸ are identical or different and are each independently of the other hydrogen, (C₁ -C₄)-alkyl and/or (C₁ -C₄)-acyl;

R¹⁹⁹ is (C₁ -C₁₀)-alkyl, phenyl or substituted phenyl; wherein in (C₁ -C₁₂)-alkyl, (C₁ -C₁₂)-alkoxy, (C₁ -C₁₂)-alkylthio and (C₂ -C₁₂)-alkenyl one or more, preferably up to 3, CH₂ groups may be replaced by hetero atom radicals such as O, S, SO, SO₂, NR^(10') or SiR^(11') R^(12') ; R^(10'), R^(11') and R^(12') have the meanings of R¹⁰, R¹¹, R¹² ;

the (C₁ -C₁₂)-alkyl radical with or without the abovementioned variations may also be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group below consisting of halogen, halo-(C₁ -C₄)-alkoxy, hydroxyl, (C₃ -C₈)-cycloalkyl, (C₃ -C₈)-cycloalkenyl, (C₁ -C₄)-acyl, phenoxy, substituted phenoxy, phenyl, substituted phenyl, phenylthio and substituted phenylthio; in the (C₁ -C₇)-alkoxy and (C₁ -C₇)-alkylthio radicals, one or more, preferably up to three, CH₂ groups may be replaced by O, and these radicals may be substituted by one or more, preferably up to three (in the case of halogen up to the maximum number), identical or different radicals selected from the group consisting of halogen, phenyl, substituted phenyl, (C₃ -C₈)-cycloalkyl, (C₃ -C₈)-cycloalkenyl, phenoxy and substituted phenoxy; or, if not included in the above definitions the definitions the carbon containing groups defined under R⁶, R⁷ or R⁸, it can be substituted by one or more, preferably up to three (in the case of halogen up to the maximim number of the same or different groups selected from halogen, cycloalkyl, phenoxy, substituted phenoxy, phenyl or substituted phenyl.

An inorganic anion is an anion of an inorganic acid, for example F--, Cl--, Br--, I--, NO₃ --, SO₄ ² --, HSO₄ --, PO₄ ³ --, HPO₄ ² --, H₂ PO₄ --, PO₃ ³ -- or N₃ --, or a complex anion, for example BF₄ --, PF₆ -- or tetraphenylborate.

An organic anion is an anion of an organic acid (carboxylic acid, sulfonic acid, phosphonic acid and the like) or an aromatic or heteroaromatic phenol-like compound. These are, for example, anions of mono- or bifunctional carboxylic acids and hydroxycarboxylic acids such as acetic acid, propionic acid, maleic acid, succinic acid, glycolic acid, oxalic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and sulfonic acids such as p-toluenesulfonic acid, dodecylsulfonic acid or 1,5-naphthalenedisulfonic acid, or saccharine.

If A and D are part of a pyrimidine system, it is assumed that A is nitrogen and D is N⁺ R. However, it cannot be excluded with absolute certainty that the radical R is in position 3 (i.e. that A is N⁺ R and D is nitrogen).

Preferred compounds of formula I are those in which

R¹ is hydrogen, halogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl or (C₃ -C₅)-cycloalkyl;

R² and R³ are identical or different and are each hydrogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₂ -C₄)-alkenyl, (C₂ -C₄)-haloalkenyl, (C₂ -C₄)-alkynyl, (C₂ -C₄)-haloalkynyl, trimethylsilylalkynyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-haloalkoxy, (C₁ -C₄)-alkoxy-(C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkoxy-(C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy-(C₁ -C₄)-haloalkyl, (C₁ -C₄)-haloalkoxy-(C₁ -C₄)-haloalkyl, halogen, hydroxy, (C₁ -C₄)-hydroxyalkyl, (C₁ -C₄)-alkanoyl, (C₁ -C₄)-haloalkanoyl, (C₃ -C₅)-cycloalkyl, (C₃ -C₅)-halocycloalkyl, cyano, (C₁ -C₄)-cyanoalkyl, nitro, (C₁ -C₄)-nitroalkyl, thiocyanato, (C₁ -C₄)-thiocyanatoalkyl, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₄)-alkoxycarbonyl-(C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkoxycarbonyl, (C₁ -C₄)-alkylthio, (C₁ -C₄)-alkylthio-(C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkylthio, (C₁ -C₄)-alkylsulfinyl, (C₁ -C₄)-haloalkylsulfinyl, (C₁ -C₄)-alkylsulfonyl (C₁ -C₄)-haloalkylsulfonyl; amino, (C₁ -C₄)-alkylamino or C₁ -C₄)-dialkylamino

R² and R³ together with the linking carbon atoms form an unsaturated 5- or 6-membered carbocyclic ring which, if it is a 5-membered ring, may contain an oxygen or sulfur atom in the place of a CH₂ or which, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, preferably trifluoromethyl, halogen, (C₁ -C₄)-alkoxy or (C₁ -C₄)-haloalkoxy; or

R² and R³ together with the linking carbon atoms form a 5-, 6- or 7-membered alicyclic ring which may contain oxygen and/or sulfur in the place of one or two carbon ring members and which is, if desired, substituted by 1, 2 or 3 (C₁ -C₄)-alkyl groups.

It is also preferred that

R¹ is hydrogen, methyl, fluorine or chlorine;

R² and R³ are each hydrogen, (C₁ -C₄)-alkyl, (C₂ -C₄)-alkenyl, (C₂ -C₄)-alkynyl, amino, (C₁ -C₄)-alkylamino, (C₁ -C₄)-dialkylamino, trimethysilylethynyl, methoxycarbonyl, (C₁ -C₄)-haloalkyl, (C₂ -C₄)-haloalkenyl, methoxy, ethoxy, halogen, methoxymethyl or cyano; or

R² and R³ join with the linking carbon atoms to form an unsaturated 5- or 6-membered ring with or without substitution which may, in the case of the 5-membered ring, contain a sulfur atom instead of a CH₂ unit; or

R² and R³ join with the linking carbon atoms to form a saturated 5- or 6-membered ring which may contain a sulfur or oxygen atom instead of a CH₂ unit;

X is NH or oxygen.

Similarly preferred compounds are those in which

R⁴ and R^(4') are hydrogen, fluorine, chlorine; methyl or trifluoromethyl, especially e hydrogen or methyl

q is preferably 0 to 1, especially 1, whereby the aromatic ring system on the cycloalkyl group is cis or trans to the X group and in the case that the cycloalkyl group is cyclohexyl (n=1) and the above preferred units are in the 1,4 position then the cis configuration is preferred.

l is preferably 1 or 2 and m is preferably 0 or 1.

Each R⁹ which may be the same or different from any other R⁹ substituent is preferably (C₂ -C₄)-haloalkenyloxy, (C₂ -C₄)-haloalkynyloxy, (C₁ -C₄)-haloalkoxy-(C₁ -C₄)-haloalkoxy, oxiran-2-ylmethoxy, oxetan-2-ylmethoxy, hydroxy, heterocyclyoxy, in which the heterocyclyloxy can be substituted with up to 3 and, in the case of fluorine up to the maximum amount, of the same or different substituents D¹ R¹², cyano, nitro or halogen or R⁹ is Z--R¹¹, Z is OSO₂, OSO₂ NR¹³, U¹ P (W¹) V¹ V² or U C(W)V; and

U, U¹ and W are oxygen,

V, V¹ and V² are a direct bond, NR¹³, oxygen, in which R¹³ is hydrogen (C₁ -C₄)-alkyl or (C₁ -C₄)-alkanoyl in which on the V¹ and V² groups is a group R¹¹ which together with the phosphorus atom can form a cyclic group, such as ##STR4## R¹¹ is (C₁ -C₈)-alkyl, aryl (C₁ -C₂)-alkyl, (C₂ -C₈)-alkenyl, (C₂ -C₈)-alkynyl, (C₃ -C₈)-alkynyl, (C₃ -C₈)-cycloalkyl, (C₄ -C₈)-cycloalkenyl and these groups can be optionally substituted with up 3 and in the case of fluorine up to the maximum amount of the same or different groups D² R¹⁴ or R¹¹ is aryl or heterocyclyl in which both groups are unsubstituted or can be substituted with up to 3 and, in the case of fluorine, up to the maximum amount of the same or different groups D³ R¹⁵ or

each R¹⁰ which can be the same or different from any other R¹⁰ group is hydrogen, cyano, nitro, halogen, (C₁ -C₄)-alkyl, (C₁ -C₂)-haloalkyl or (C₂ -C₄)-alkenyl or 2 adjacent groups R⁹ and/or R¹⁰ together with carbon atom to which they are attached can form an unsaturated 6-membered carbocyclic ring or 2 adjacent groups R⁹ and/or R¹⁰ together with a carbon atom to which they are attached can form a saturated 5 or 6-membered, cyclic ring which a CH₂ group can be replaced by an oxygen or sulphur.

Particularly preferred are compounds of formula 1 in which

R¹ is hydrogen or methyl and

R² and R³ are hydrogen, methyl, ethyl, propyl, methoxy, (C₂ -C₃)-alkenyl, amino, (C₁ -C₄)-alkylamino, di-(C₁ -C₄)-alkylamino, (C₂ -C₃ -chloro- or fluoro-alkenyl (C₂ -C₃)-alkynyl, trimethylsilylethynyl, (C₂ -C₃)-chloro- or fluoro-alkyl, methoxymethyl, halo or cyano or

R² and R³ together with a ring system to which they are bound can form a quinazoline or quinoline system in which the carbocylic part can be substituted by fluorine or

R² and R³ together with the carbon atoms to which they are attached can form a saturated 6-membered ring which in place of the CH₂ group can contain an oxygen or sulphur atom.

Particularly preferred compounds are those wherein

R¹ is hydrogen or methyl,

R² is methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, (C₁ -C₂)-fluoroalkyl or methoxymethyl,

R³ is fluorine, chlorine, bromine, cyano, vinyl, ethynyl, (C₁ -C₂)-fluoroalkyl, amino, (C₁ -C₂)-alkylamino (C₁ -C₂)-dialkylamino or methoxy or in the case that A is nitrogen,

R² and R³ together with a ring system to which they are formed can form a quinazoline group which can be substituted with fluorine and

X is NH.

Also preferred are compounds of formula I, in which

R⁴ and R^(4') are hydrogen,

q is 1 whereby in the aromatic system attached to the 4 position of the cyclohexyl group is in the cis configuration in relation to X,

l is 1 and m is 0,

R⁹ is defined above and

each R¹⁰ independently of each other are hydrogen, methyl, cyano, nitro, fluorine or chlorine.

Even more preferred are compounds of formula I in which

R¹ is hydrogen,

R² is ethyl or methoxymethyl,

R³ is fluorine, chlorine, bromine or methoxy and especially R² =ethyl, and R³ =chlorine,

A is nitrogen,

X is NH,

R⁴ and R^(4') are H,

R⁹ is as defined above and is preferably in the 4 position of the aromatic ring whereby the aromatic group on the cyclohexane ring and the substituent X are in the cis configuration in relation to each other,

R¹⁰ is hydrogen.

Of these, preferred compounds are those in which

R⁹ is (C₂ -C₄)-haloalkenyloxy, (C₂ -C₄)-haloalkynyloxy, oxetan-2-ylmethoxy, hydroxy, heterocyclyloxy, heterocyclyoxy substituted with D¹ R¹², cyano nitro or halo or is a group ZR¹¹, in which

Z is OSO₂, U¹ P (W¹) V¹ V² or UC(W)V and

W is oxygen,

W¹ is oxygen or sulphur,

V, V¹ and V² are a direct bond, NR¹³ or oxygen in which R¹³ is hydrogen or (C₁ -C₄)-alkyl,

R¹¹ is (C₁₋₄)-alkyl, aryl CH₂ --(C₂₋₄)-alkenyl, (C₂ -C₄)-alkynyl, (C₃ -C₆)-cycloalky and these groups can optionally be substituted by up to 3 and, in the case of fluorine up to the maximum amount, of the same or different groups D³ R¹⁵, or

R¹¹ is aryl or heterocyclyl in which both these groups are unsubstituted or substituted with up to 3 and, in the case of fluorine up the maximum amount, of the same or different groups D³ R¹⁵ or in which

D¹, D² and D³ independently of each other are a direct bond or oxygen

R¹², R¹⁴ and R¹⁵, independently of each other, are hydrogen, cyano, nitro, halogen, (C₁₋₄)-alkyl, (C₁₋₄)-haloalkyl, (C₂ -C₄)-alkenyl, (C₂ -C₄)-haloalkenyl, (C₂ -C₄)-alkynyl, (C₂ -C₄)-haloalkynyl, (C₃ -C₆)-cycloalkyl, (C₄ -C₆)-cycloalkenyl, aryl, heterocyclyl, whereby in the last named 4 groups the cycloaliphatic, aromatic or heterocyclic ring system are unsubstituted or substituted with up to 3, and in the case of fluorine up to the maximum amount, of the same or different substituents of R¹⁸, in which

R¹⁸ is (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₁₋₄)-alkoxy, (C₁ -C₄)-haloalkoxy, cyano, nitro or halogen.

It is also preferred that

A is nitrogen and D is N⁺ R or nitrogen; and

Q^(n-) is an anion, such as Hal⁻, NO₃ ⁻, BF₄ ⁻, BPh₄ ⁻ or PF₆ ⁻ ;

In the above formula I, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, 2 to 6 carbon atoms, are preferred for these radicals. alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyl radicals, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. cycloalkyl is a carbocyclic saturated ring system preferably having 3-8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl, but also bicyclic systems, for example the norbornyl group, the bicyclo[2.2.2]octane radical and tricyclic systems, for example adamantyl.

halogen is, for example, fluorine, chlorine, bromine or iodine. haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example monohaloalkyl, perhaloalkyl, CF₃, CHF₂, CH₂ F, CF₃ CF₂, CH₂ FCHCl, CCl₃, CHCl₂, CH₂ CH₂ Cl; haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂ F, CF₃ CF₂ O, OCH₂ CF₃ and OCH₂ CH₂ Cl; the same applies analogously to haloalkenyl and other halogen-substituted radicals.

A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl. Preferably, a hydrocarbon radical is alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl. The same applies analogously to a hydrocarbon radical in a hydrocarbonoxy radical.

aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.

A heterocyclic radical or ring (heterocycle) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, i.e. hetero atoms or ring members, including substituted hetero atoms, preferably selected from the group consisting of N, O, S, SO, SO₂ ; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and it contains 1, 2 or 3 hetero units. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl), for example a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, in particular an aromatic system in which at least 1, preferably up to 4, in particular up to 2 CH are replaced by N and/or at least 1, preferably up to 3, --CH═CH-units is replaced by NH, S or O adjacent oxygen atoms being excluded, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, pyrrolidinyl, piperidinyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally oxo. The oxo group can also be present on the hetero ring atoms, which can exist at various oxidation levels, for example in the case of N and S.

Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl or heteroaryl, are, for example, a substituted radical derived from the unsubstituted skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl, cycloalkyl and haloalkyl; the term "substituted radicals" such as substituted alkyl etc. includes as substituents, in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., with or without substitution. Preferred among the radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred substituents are generally selected from the group consisting of halogen, for example fluorine and chlorine, (C₁ -C₄)-alkyl, preferably methyl or ethyl, (C₁ -C₄)-haloalkyl, preferably trifluoromethyl, (C₁ -C₄)-alkoxy, preferably methoxy or ethoxy, (C₁ -C₄)-haloalkoxy, nitro and cyano. Especially preferred are the substituents methyl, methoxy and chlorine.

Mono- or disubstituted amino is a chemically stable radical selected from the group consisting of the substituted amino radicals which are N-substituted, for example by one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino and N-heterocycles; preference is given to alkyl radicals having 1 to 4 carbon atoms; aryl is preferably phenyl or substituted phenyl; acyl is defined as indicated further below and is preferably (C₁ -C₄)-alkanoyl. The same applies analogously to substituted hydroxylamino or hydrazino.

Unsubstituted or substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably up to trisubstituted, by identical or different radicals selected from the group consisting of halogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-haloalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyl radicals, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

An acyl radical is the radical of an organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, iminocarboxylic acids with or without N-substitution, or the radical of carbonic monoesters, carbamic acid with or without N-substitutien, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids. acyl is, for example, formyl, alkylcarbonyl such as [(C₁ -C₄)alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids. In each case, the radicals may be substituted even further in the alkyl or phenyl moiety, for example in the alkyl moiety by one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents in the phenyl moiety are the substituents already mentioned further above in general for substituted phenyl.

Furthermore, in the above formulae the term "dimethyl-(C₁ -C₈)-alkylsilylethynyl" denotes, for example, the trimemethylsilylethynyl or the tert-butyldimethylsilylethynyl group;

the term "(C₁ -C₄)-hydroxyalkyl" denotes, for example, the hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxy-1-methylethyl or the 1-hydroxypropyl group;

the term "(C₁ -C₄)-alkanoyl" denotes, for example, the formyl, acetyl, propionyl, 2-methylpropionyl or butyryl group;

the term "(C₁ -C₁₂)-alkanoyl" denotes, for example, the abovementioned radicals and, for example, the valeroyl, pivaloyl, hexanoyl, decanoyl or the dodecanoyl group;

the term "(C₂ -C₄)-haloalkanoyl" denotes a (C₁ -C₄)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine;

the term "(C₂ -C₁₂)-haloalkanoyl" denotes a (C₁ -C₂₀)-alkanoyl group in which the hydrogen atoms are partly, in the case of fluorine partly or wholly, replaced by halogen atoms, preferably fluorine or chlorine;

the term "cyano-(C₁ -C₄)-alkyl" denotes a cyanoalkyl group whose hydrocarbon radical has the meanings given for the term "(C₁ -C₄)-alkyl";

the term "(C₁ -C₄)-alkylamino" denotes, for example, methylamino, ethylamino, isopropylamino;

the term "(C₁ -C₄)-dialkylamino" denotes, for example, dimethylamino, N-ethyl-N-methylamino, diethylamino,

the term "(C₁ -C₄)-alkoxycarbonyl" denotes, for example, the methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl or tert-butoxycarbonyl group;

the term "(C₁ -C₁₂)-alkoxycarbonyl" denotes the abovementioned radicals and, for example, the hexyloxycarbonyl, 2-methylhexyloxycarbonyl, decyloxycarbonyl or dodecyloxycarbonyl group;

the term "(C₁ -C₄)-haloalkoxycarbonyl" denotes a (C₁ -C₄)-alkoxycarbonyl group in which one or more, in the case of fluorine possibly all, hydrogen atoms are replaced by halogen, preferably fluorine or chlorine;

the term "(C₁ -C₄)-haloalkylthio" denotes a (C₁ -C₄)-alkylthio group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine;

the term "(C₁ -C₄)-alkylsulfinyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group;

the term "(C₁ -C₄)-alkylsulfonyl" denotes, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group;

the terms "(C₁ -C₄)-haloalkylsulfinyl" and "(C₁ -C₄)-haloalkylsulfonyl" denote (C₁ -C₄)-alkylsulfinyl and -sulfonyl radicals having the abovementioned meanings in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular chlorine or fluorine;

the term "(C₁ -C₄)-alkoxy-(C₁ -C₄)-alkyl" denotes, for example, a 1-methoxyethylene group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a methoxymethyl or ethoxymethyl group, a 3-methoxypropyl group or a 4-butoxybutyl group;

the terms "(C₁ -C₄)-haloalkoxy-(C₁ -C₄)-alkyl", "(C₁ -C₄)-alkoxy-(C₁ -C₄)-haloalkyl" and "(C₁ -C₄)-haloalkoxy-(C₁ -C₄)-haloalkyl" denote (C₁ -C₄)-alkoxy-(C₁ -C₄)-alkyl radicals having the abovementioned meanings where one or more, in the case of fluorine possibly all, hydrogen atoms of the appropriate hydrocarbon moieties are replaced by halogen, preferably chlorine or fluorine;

the term "(C₁ -C₄)-alkylthio-(C₁ -C₄)-alkyl" denotes, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl or 3-methylthiopropyl;

the term "arylthio" denotes, for example, the phenylthio or the 1- or 2-naphthylthio group;

the term "aryloxy" denotes, for example, the phenoxy- or 1- or 2-naphthyloxy group;

the term "heterocyclyloxy" or "heterocyclylthio" denotes one of the abovementioned heterocyclic radicals which are linked via an oxygen or sulfur atom;

the term "cycloalkoxy" or "cycloalkylthio" denotes one of the abovementioned cycloalkyl radicals which are linked via an oxygen or sulfur atom;

the term "aroyl" denotes, for example, the benzoyl, naphthoyl or the biphenylcarbonyl group;

the term "aryl-(C₁ -C₄)-alkanoyl" denotes, for example, the phenylacetyl, 3-phenylpropionyl, 2-phenylpropionyl, 2-methyl-2-phenylpropionyl, 4-phenylbutyryl or the naphthylacetyl group;

the term "(C₃ -C₈)-cycloalkyl-(C₁ -C₄)-alkanoyl" denotes, for example, the cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclohexylacetyl or the cyclohexylbutyryl group;

the term "heterocyclyl-(C₁ -C₄)-alkanoyl" denotes, for example, the thenoyl, furoyl, nicotinoyl, thienylacetyl or the pyridinepropionyl group;

the term "(C₃ -C₈)-cycloalkoxycarbonyl" denotes, for example, the cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl or the cycloheptyloxycarbonyl group;

the term "(C₃ -C₈)-cycloalkyl-(C₁ -C₄)-alkoxycarbonyl" denotes, for example, the cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentyloxymethoxycarbonyl, cyclohexyloxymethoxycarbonyl, 1-(cyclohexyl)-ethoxycarbonyl or the 2-(cyclohexyl)ethoxycarbonyl group;

the term "aryl-(C₁ -C₄)-alkoxycarbonyl" denotes, for example, the benzyloxycarbonyl, 1-naphthylmethoxycarbonyl, 2-naphthylmethoxycarbonyl, 1-phenylethoxycarbonyl or the 2-phenylethoxycarbonyl group;

the term "heterocyclyl-(C₁ -C₄)-alkoxycarbonyl" denotes, for example, the thienylmethoxycarbonyl, furylmethoxycarbonyl, tetrahydrofurylmethoxycarbonyl or the pyridylethoxycarbonyl group;

the term "aryloxycarbonyl" denotes, for example, the phenoxycarbonyl, naphthoxycarbonyl or the biphenyloxycarbonyl group;

the term "heterocyclyloxycarbonyl" denotes, for example, the tetrahydropyran-4-oxycarbonyl group;

the term "(C₁ -C₂₀)-alkanoyloxy" denotes, for example, the formyloxy, acetoxy, propionyloxy, butyryloxy, pivaloyloxy, valeroyloxy or the hexanoyloxy group;

the term "(C₂ -C₂₀)-haloalkanoyloxy" denotes a (C₂ -C₂₀)-alkanoyloxy group in which one or more, in the case of fluorine possibly all, hydrogen atoms of the hydrocarbon moiety are replaced by halogen, in particular fluorine or chlorine;

the term "(C₃ -C₈)-cycloalkanoyloxy" denotes, for example, the cyclopropanoyloxy, cyclobutenoyloxy, cyclopentanoyloxy, cyclohexanoyloxy or the cycloheptanoyloxy group;

the term "(C₃ -C₈)-cycloalkyl-(C₁ -C₄)-alkanoyloxy" denotes, for example, the cyclopropylcarbonyloxy, cyclopropylacetoxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cyclohexylacetoxy or the 4-cyclohexylbutyryloxy group;

the term "aroyloxy" denotes, for example, the benzoyloxy or the naphthoyloxy group;

the term "aryl-(C₁ -C₄)-alkanoyloxy" denotes, for example, the benzoyloxy, naphthoyloxy, biphenylcarbonyloxy, phenylacetoxy or the phenylbutyryloxy group;

the term "heterocyclyl-(C₁ -C₄)-alkanoyloxy" denotes, for example, the thienylcarbonyloxy, thienylacetoxy, pyridylcarbonyloxy or the pyrimidinylcarbonyloxy group;

the term "(C₁ -C₂₀)-alkylsulfonyloxy" denotes, for example, the methane-, ethane-, butane- or hexanesulfonyloxy group;

the term "arylsulfonyloxy" denotes, for example, the phenylsulfonyloxy or the toluenesulfonyloxy group;

a bivalent hydrocarbon chain denotes a radical which is derived from n-alkanes or n-alkenes by removal of in each case one hydrogen atom from each of the two terminal carbon atoms of the chain, such as methylene, ethanediyl, trimethylene, tetramethylene;

the term (C₁ -C₁₈)-alkanediyldioxy denotes a bivalent radical derived from (C₁ -C₁₈)-alkanes by replacement of two hydrogen atoms by two --O-- radicals.

The illustration given above applies correspondingly to homologues or to radicals derived therefrom.

In addition to the cis/trans isomerism mentioned, some of the compounds of the formula I have one or more asymmetric carbon atoms or stereoisomers at double bonds. Enantiomers or diastereomers may therefore be present. The invention embraces both the pure isomers and mixtures thereof. Mixtures of diastereomers can be separated into the components by conventional methods, for example by selective crystallisation from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by conventional methods, for example by salt formation with an optically active acid, separation of the diastereomeric salts and liberation of the pure enantiomers using a base.

The invention furthermore relates to a process for preparing compounds of the formula I which comprises reacting a compound of the formula II ##STR5## where R¹, R² and R³ have the meanings given above, A is CH or N and L is a leaving group, for example halogen, alkylthio, alkanesulfonyloxy or arylsulfonyloxy, alkylsulfonyl or arylsulfonyl, with a nucleophile of formula III ##STR6## where X, q, R⁴, R^(4') and R⁵ are as defined under formula I, and, if desired, converting the compound of the formula I obtained in this manner or in another manner, into its N-oxide and/or salt and optionally the nitrogen heterocycle or the side chain R⁵ can be derivatised in known manner

A typical reaction scheme is as follows ##STR7##

The substitution reaction described above is known in principle. The leaving group L can be varied within wide limits and can be, for example, a halogen atom, such as fluorine, chlorine, bromine or iodine; or alkylthio, such as methyl- or ethylthio; or alkylsulfonyloxy, such as methane-, trifluoromethyl- or ethylsulfonyloxy; or arylsulfonyloxy, such as benzenesulfonyloxy; or toluenesulfonyloxy, or alkylsulfonyl such as methyl- or ethylsulfonyl; or arylsulfonyl such as phenyl- or toluenesulfonyl.

The abovementioned reaction is carried out in a temperature range from 20-150° C., advantageously in the presence of a base and, if appropriate, in an inert organic solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidin-2-one, dioxane, tetrahydrofuran, 4-methyl-2-pentanone, methanol, ethanol, butanol, ethylene glycol, ethylene glycol dimethyl ether, toluene, chlorobenzene or xylene. It is also possible to employ mixtures of these solvents.

Suitable bases in the case where X is oxygen are, for example, alkali metal or alkaline earth metal carbonates, bicarbonates, amides or hydrides, such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium amide or sodium hydride, and in the case where X is NH, these are, for example, alkali metal or alkaline earth metal carbonates, bicarbonates, hydroxides, amides or hydrides such as sodium carbonate, sodium bicarbonate, potassium carbonate, sodium hydroxide, sodium amide or sodium hydride, or organic bases, such as triethylamine or pyridine, or else a second equivalent of the nucleophile where X═NH.

The compounds of the formula II required as starting materials are in most cases known from the literature or can be prepared by methods similar to those that are known (cf. EP-A-370 391, EP-A-470 600, DE-A-43 31 179, DE-A-44 04 702).

To prepare the nucleophiles of the formula III, suitably substituted cyclopentanones, cyclohexanones or cycloheptanones which are either known commercially or can be obtained in known manner are converted into the corresponding amines by reductive amination (H₂, NH₃, metal catalyst or ammonium acetate/sodium cyanoborohydride) or by a Leuckart-Wallach reduction) or into the corresponding alcohols by reduction with a complex metal hydride. For the preparation of the especially preferred cis derivatives this can be done suitably by reductive amination especially using a rhodium or a rhodium/palladium mixed catalyst, and as the complex metal hydride especially suitable are those which besides the hydrogen carry bulky alkyl substituents, such as for example L-Selectride.

Alternatively, there is the possibility that cycloalkanones, can be reduced with a complex metal hydride (LiAlH₄, NaBH₄) to the corresponding alcohols, and from these via the mesylate or tosylate (CH₃ SO₂ Cl/CH₃ C₆ H₄ SO₂ Cl, pyridine) and azide (NaN₃, DMF) to obtain the amine (H2/Pd or LiAlH₄) (see C. D. Lednicer, D. E. Emmert, R. Lakti, A. D. Rudzik, J. Med. Chem. 15, 1239, (97-2). The chosen alcohols can be obtained also directly from aldehydes and glycerines with acid catalysis (P. E. Verkade, J. D. van Roon, Rec. Trav. Chim. Holland, 61, 831 (1942); E. Juaristi, S. Antunez, Tetrahedron 48, 5941 (1992)).

Compounds of formula I in which A or D have the meaning N⁺ R×1/nQ^(n-) can be obtained in known methods by quaternisation of the compounds of formula I in which A is CH or N and D is N (e.g. as described in our DE 19647402, 19647413 1967317 and 19719590.

While being tolerated well by plants and having favourable toxicity toward warm-blooded animals, the active substances are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and very particularly preferably for controlling insects and arachnids, which are encountered in agriculture, in animal breeding, in forestry, in the protection of stored products and materials, and in the hygiene sector. They are active against normally sensitive and resistant species and against all or certain stages of development. The abovementioned pests include:

From the order of the Acarina, for example Acarus siro, Argas spp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

From the order of the isopoda, for example Oniscus asselus, Armadium vulgar and Porcellio scaber.

From the order of the Diplopoda, for example Blaniulus guttulatus.

From the order of the Chilopoda, for example Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example Scutigerella immaculata.

From the order of the Thysanura, for example Lepisma saccharina.

From the order of the Collembola, for example Onychiurus armatus.

From the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea madeirae, Blatella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the isoptera, for example Reticulitermes spp.

From the order of the Anoplura, for example Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example Trichodecte spp. and Damalinea spp.

From the order of the Thysanoptera, for example Hercinothrips femoralis, Thrips tabaci and Frankliniella spp.

From the order of the heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arandinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cuaphalocrocis spp. and Manduca spp.

From the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonumus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogorma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conorus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica and Lissorhoptus spp.

From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hyporma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the order of the Siphonaptera, for example Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example Scorpio maurus and Latrodectus mactans.

From the class of the helminths, for example Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola.

From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp.

From the class of the Bivalva, for example Dreissena spp.

The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterora and Globora (cyst-forming nematodes, such as Globora rostochiensis, Globora pallida, heterora trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni), Rotylenchus (such as Rotylenchus robustus), Helicotylenchus (such as Helicotylenchus multicinctus), Belonoaimus (such as Belonoaimus longicaudatus), Longidorus (such as Longidorus elongatus), Trichodorus (such as Trichodorus primitivus) and Xiphinema (such as Xiphinema index).

The compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destriuctor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici).

The invention also relates to compositions, especially insecticidal and acaricidal compositions, which comprise the compounds of the formula I in addition to suitable formulation auxiliaries.

The compositions according to the invention comprise the active substances of the formulae I in general in a proportion of from 1 to 95% by weight. They can be formulated in various ways depending on the biological and/or chemicophysical parameters which prevail. Possible formulations which are suitable are therefore:

wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusts (DP), seed-dressing products, granules in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in:

Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, "Pesticides formulations", Marcel Dekker N.Y., 2nd ed. 1972-73; K. Martens, "Spray Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in:

Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, N.Y.; Marsden, "Solvents Guide", 2nd ed., lnterscience, N.Y. 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1967; Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to produce combinations with other pesticidally active substances, fertilisers and/or growth regulators, for example in the form of a ready-mix or a tank mix. Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active substance and in addition to a diluent or inert material, wetting agents, for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate. Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. As emulsifiers, the following can be used, for example: calcium salts of alkylaryl-sulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusts are obtained by grinding the active substance with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can be prepared either by atomizing the active substance onto adsorptive, granulated inert material or by applying active substance concentrates onto the surface of carrier materials such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active substances can also be granulated in the fashion conventional for the preparation of fertilizer granules, if desired as a mixture with fertilisers.

In wettable powders, the concentration of active substance is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active substance may be from approximately 5 to 80% by weight. Dust formulations comprise in most cases from 5 to 20% by weight of active substance, sprayable solutions from about 2 to 20% by weight. In the case of granules, the content of active substance depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.

In addition, the abovementioned formulations of active substance comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.

The concentrates, which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.

The application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active substance, but is preferably between 0.001 and 5 kg/ha.

The active substances according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active substances, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.

The active substance content of the use forms prepared from the commercially customary formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.

Application is effected in a conventional fashion, matched to the use forms.

The active substances according to the invention are also suitable for controlling ecto- and endoparasites in the veterinary medicine sector or in the sector of animal husbandry.

The active substances according to the invention are in this case applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.

The novel compounds, according to the invention, of the formula I can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.). In a preferred embodiment of the invention, the novel compounds, if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since they are excreted in active form in the droppings, the development of insects in the animal droppings can be prevented very simply in this fashion. The dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods. In the case of cattle, the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.

Some compounds of the formula I according to the invention are also distinguished by an fungicidal action. Fungal pathogens which have already penetrated the plant tissue can be successfully subjected to curative control. This is particularly important and advantageous in the case of those fungal diseases which can no longer be controlled effectively with the otherwise customary fungicides when infection has taken place already. The spectrum of action of the claimed compounds embraces various economically important phytopathogenic fungi, for example Plasmopara viticola, Phytophthora infestans, Erysiphe graminis, Pyricularia oryzae, Pyrenophora teres, Leptosphaeria nodorum, Pellicularia sasakii and Puccinia recondita.

In addition, the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.

The active substances according to the invention in their commercially customary formulations can be employed either alone or in combination with other fungicides known from the literature.

The abovementioned components for combinations are known active substances of which many are described in The Pesticide Manual, edited by C D S Tomlin, 11th edition (1997), bublished by the British Crop Protection Council. The active substance content of the use forms prepared from commercially customary formulations can vary within wide limits, and the concentration of active substance in the use forms can be from 0.0001 up to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. The formulations are applied in a customary manner adapted to suit the use forms.

The examples which follow illustrate the invention without limiting it thereto.

A. FORMULATION EXAMPLES

a) A dust is obtained by mixing 10 parts by weight of active substance and 90 parts by weight of talc as inert material and comminuting in a hammer mill.

b) A wettable powder which is easily dispersible in water is obtained by mixing 25 parts by weight of active substance, 65 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurinate as wetting and dispersing agent, and grinding in a pinned disk mill.

c) A dispersion concentrate which is easily dispersible in water is prepared by mixing 40 parts by weight of active substance with 7 parts by weight of a sulfosuccinic monoester, 2 parts by weight of a sodium ligninsulfonate and 51 parts by weight of water and grinding in a ball mill to a fineness of below 5 microns.

d) An emulsifiable concentrate can be prepared from 15 parts by weight of active substance, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of ethoxylated nonylphenol (10 EO) as emulsifier.

e) Granules can be prepared from 2 to 15 parts by weight of active substance and an inert granule carrier material such as attapulgite, granulated pumice and/or quartz sand. It is advantageous to use a suspension of the wettable powder of Example b) with a solids content of 30% which is sprayed onto the surface of attapulgite granules which are then dried and intimately mixed. The proportion by weight of the wettable powder in this case is about 5% and that of the inert carrier material is about 95% of the finished granules.

B. PREPARATION EXAMPLES Example 1 ##STR8## 5-Chloro-6-ethyl-4-[cis-4-(4-hydroxy)phenylcyclohexylamino]pyrimidine

9.3 g 4,5-dichloro-6-ethylpyrimidine, 10 g cis-4-(4-hydroxyphenylcyclohexylamine and 15 ml triethylamine were heated in 100 ml dimethylformamide at 80° C. for 7 hours. The mixture was poured into water and stirred for 0.5 hours at 25° C. The resulting crystals were separated, washed once with a small amount of cold ethyl acetate and dried in vacuo to give the title product, m.p. 228° C. (compound 1).

Example 2 ##STR9## 5-Chloro-6-ethyl-4-[cis-4-(4-trifluoromethylsulfonyloxy)phenylcyclohexylamino]-pyrimidine

1.36 g triethylamine were added at 10° C. to a solution of 3.00 g of compound 1 and 3.3 g trifluoromethanesulfonic acid anhydride in 30 ml of dichloromethane. The reaction mixture was stirred for 4 hours at 25° C. and then quenched with water. The organic layer was dried with sodium sulfate and the solvent was removed under reduced pressure. Chromatography (silica gel, ethyl acetate) gave the title product as a yellowish oil (compound 2).

Example 3 ##STR10## 5-Chloro-6-ethyl-4-[cis-4-(4-trifluoromethylsulfonyloxy)phenylcyclohexylamino]-1-(benzoyloxymethyl)pyrimidinium iodide

0.7 g of compound 2, 0.3 g of chloromethyl benzoate and 0.23 g of sodium iodide in 20 ml of acetonitrile were heated under reflux for 12 hours. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried with sodium sulfate and the solvent removed. Chromatography (silica gel, ethyl acetate/methanol) gave the title product, m.p. 184° C. (Compound 3)

Example 4 ##STR11## 5-Chloro-6-ethyl-4-[cis4-[4-(5-trifluoromethylpyrid-2-yloxy)phenyl]-cyclohexylamino]pyrimidine

3.5 g 4,5-dichloro-6-ethyl-pyrimidine, 6.7 g 4-(5-trifluoromethyl-pyrid-2-yloxy)phenyl]cyclohexylamine and 3.0 g triethylamine were heated without solvent at 80-90° C. for 6 hours. The mixture was taken up in water/dichloromethane and the organic phase was dried and concentrated. For purification and for the separation of the cis/trans isomers, the residue was chromatographed over silica gel with ethyl acetate/petroleum ether (7:3), to give the title product, m.p. 114-6° C.). (Compound 4)

Preparation of the Starting Materials

4-(5-trifluoromethylpyrid-2-yloxy)phenyl]cyclohexylamine

33.5 g 4-(5-trifluoromethylpyrid-2-yloxy)phenyl]cyclohexanone and 38.5 g ammonium acetate were dissolved in 350 ml of methanol and stirred for 30 minutes. 31.4 g sodium cyanoborohydride was added portionwise at 0° C. The mixture was stirred at room temperature for 24 hours. The mixture was concentrated and the residue was taken up in toluene/dilute sodium hydroxide solution. The organic phase was dried and concentrated, to give the title product as a yellow oil, which was reacted without further purification.

4-(5-trifluoromethylpyridine-2-yloxy)phenyl]cyclohexylamine

To a suspension of 9.0 g sodium hydride (80% dispersion in mineral oil) in 300 ml of dimethylformamide was added, with cooling, a solution of 54 g 4-(4-hydroxyphenylcyclohexanone. After stirring for 30 minutes at room temperature, a solution of 54.3 g 5-trifluoromethyl-2-chloropyridine in 100 ml of dimethylformamide was added and the mixture was reheated at 90° C. for 6 hours. The mixture was concentrated and taken up in toluene/water. The toluene layer was washed twice with water, dried and concentrated. Recrystallisation of the solid residue from methanol gave the title product, m.p. 81-3° C.

The compounds of the tables below are obtained in a similar manner to one of to Examples 1 to 4.

                  TABLE 1                                                          ______________________________________                                          ##STR12##                                                                     Cmp  Het              R.sup.2   R.sup.3                                                                              m.p./° C.                         ______________________________________                                          5   3,5-diCl-2-pyridyl                                                                              Et        Cl    121-122                                   6   5-CF.sub.3 -2-pyridyl                                                                           --CH.sub.2 OMe                                                                           MeO   oil                                       7   6-MeO-pyridazin-3-yl                                                                            --CH.sub.2 OMe                                                                           MeO   135                                       8   pyrimidin-2-yl   Et        Cl    137                                       9   6-MeO-pyridazin-3-yl                                                                            Et        Cl    resin                                    10   3,6-diMe-pyrazin-2-yl                                                                           Et        Cl    163-165                                  11   2,6-diMeO-pyrimidin-4-yl                                                                        Et        Cl    resin                                    12   5-Cl-6-Et-pyrimidin-4-yl                                                                        Et        Cl    resin                                    ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR13##                                                                     Cmp      R.sup.2 R.sup.3 R.sup.9   m.p./° C.                            ______________________________________                                         13       Et      Br      --OSO.sub.2 Me                                                                           resin                                       14       Et      Br      OH        resin                                       15       Cl      Br      --OSO.sub.2 Me                                                                           227-228                                     16       Cl      Br      OH        227-228                                     ______________________________________                                    

                                      TABLE 3                                      __________________________________________________________________________      ##STR14##                                                                     Cmp R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.9               m.p./° C.                            __________________________________________________________________________      17 H  Et Cl --OSO.sub.2 Me        wax                                          18 H  Et Cl --OSO.sub.2 -p-tolyl  152                                          19 H  Et H  OH                    88                                           20 H  Et Cl --OC(═O)CH.sub.2 -(4-PhO-phenyl)                                                                 oil                                          21 H  Et Cl pyrrolidinecarbonyloxy                                                                               wax                                          22 H  Me Cl OH                    220                                          23 Cl Et Cl OH                    173                                          24 H  Et Cl --OC(═O)Me        68                                           25 H  Et Cl --OC(═O)NPr.sup.i.sub.2                                                                          oil                                          26 H  Et Cl morpholinecarbonyloxy 124                                          27 H  Et Cl phenacyloxy           147                                          28 H  Et Cl --OC(═O)OEt       102                                          29 Me Et Cl --OSO.sub.2 CF.sub.3  oil                                          30 Me Et Cl --OSO.sub.2 Me        oil                                          31 H  Et Cl --OC(═O)NHMe      107                                          32 H  Et Cl --OC(═O)OMe       wax                                          33 H  Et Cl phenylsulfonyloxy     oil                                          34 H  Et Cl 4-F-phenylsulfonyloxy wax                                          35 H  Et Cl 4-Cl-phenylsulfonyloxy                                                                               wax                                          36 H  Et Cl 2-Cl-phenylsulfonyloxy                                                                               wax                                          37 H  Et Cl 4-tBu-phenylsulfonyloxy                                                                              84                                           38 H  Et Cl ethylsufonyloxy                                                    39 H  Et Cl 4-(acetamido)phenylsulfonyloxy                                     40 H  Et Cl 2,4-diCl-phenylsulfonyloxy                                                                           oil                                          41 H  Et Cl 3,4-diMeO-phenylsulfonyloxy                                        42 H  Et Cl 4-MeO-phenylsulfonyloxy                                                                              156-9                                        43 H  Et Cl 2-CF.sub.3 -phenylsulfonyloxy                                                                        oil                                          44 H  Et Cl 3-Cl-4-Me-phenylsulfonyloxy                                                                          oil                                          45 H  Et Cl 3-NO.sub.2 -4-Me-phenylsulfonyloxy                                 46 H  Et Cl propylsulfonyloxy     oil                                          47 H  Et Cl 3-NO.sub.2 -phenylsulfonyloxy                                                                        wax                                          48 H  Et Cl 4-NO.sub.2 -phenylsulfonyloxy                                                                        128-34                                       49 H  Et Cl 2-NO.sub.2 -phenylsulfonyloxy                                                                        wax                                          50 H  Et Cl 4-I-phenylsulfonyloxy oil                                          51 H  Et Cl isopropylsulfonyloxy                                               52 H  Et Cl 2-CF.sub.3 O-phenylsulfonyloxy                                                                       oil                                          53 H  Et Cl --OSO.sub.2 CCl.sub.3                                              54 H  Et Cl --OSO.sub.2 CCl.sub.2                                              55 H  Et Cl butylsulfonyloxy                                                   56 H  Et Cl benzylsulfonyloxy                                                  57 H  Et Cl octylsulfonyloxy                                                   58 H  Et Cl 2-NO.sub.2 -benzylsulfonyloxy                                      59 H  Et Cl 5-Br-2-thienylsulfonyloxy                                          60 H  Et Cl                                                                                 ##STR15##                                                         61 H  Et Cl --OSO.sub.2 NMe.sub.2                                              62 H  Et Cl                                                                                 ##STR16##                                                         63 H  Et Cl --OP(O)Me.sub.2                                                    64 H  Et Cl --OP(O)Et.sub.2                                                    65 H  Et Cl --OP(O)Ph.sub.2                                                    66 H  Et Cl --OP(O)(Me)Ph                                                      67 H  Et Cl --OP(O)(cyclohexyl).sub.2                                          68 H  Et Cl --OP(O)(methoxy).sub.2                                             69 H  Et Cl --OP(O)(ethoxy).sub.2                                              70 H  Et Cl --OP(O)(propoxy).sub.2                                             71 H  Et Cl --OP(O)(isopropoxy).sub.2                                          72 H  Et Cl --OP(O)(butoxy).sub.2                                              73 H  Et Cl --OP(O)(pentoxy).sub.2                                             74 H  Et Cl --OP(O)(phenoxy).sub.2                                             75 H  Et Cl --OP(O)(4-Cl-phenoxy).sub.2                                        76 H  Et Cl --OP(O)(4-toloxy).sub.2                                            77 H  Et Cl --OP(O)(NMe.sub.2).sub.2                                           78 H  Et Cl --OP(O)(NEt.sub.2).sub.2                                           79 H  Et Cl --OP(O)(NPr.sup.i.sub.2).sub.2                                     80 H  Et Cl --OP(O)(NHPh).sub.2                                                81 H  Et Cl --OP(O)(NHPh)(OPh)                                                 82 H  Et Cl --OP(S)Me.sub.2                                                    83 H  Et Cl --OP(S)Et.sub.2                                                    84 H  Et Cl --OP(S)Ph.sub.2                                                    85 H  Et Cl --OP(S)(Me)Ph                                                      86 H  Et Cl --OP(S)(OMe).sub.2                                                 87 H  Et Cl --OP(S)(OEt).sub.2                                                 88 H  Et Cl --OP(S)(OPr).sub.2                                                 89 H  Et Cl --OP(S)(OBu).sub.2                                                 90 H  Et Cl --OP(S)(NMe.sub.2).sub.2                                           91 H  Et Cl 2,4,5-triCl-phenylsulfonyloxy                                                                        wax                                          92 H  Et Cl 2-MeO--NO.sub.2 -phenylsulfonyloxy                                                                   oil                                          93 H  Et Cl 2,4,6-triMe-phenylsulfonyloxy                                                                        wax                                          94 H  Et Cl 3,4-diCl-phenylsulfonyloxy                                                                           oil                                          95 H  Et Cl 3,6-diCl-phenylsulfonyloxy                                                                           oil                                          96 H  Et Cl 3-NO.sub.2 -6-Me-phenylsulfonyloxy                                                                   oil                                          97 H  Et Cl 1-naphthylsulfonyloxy wax                                          98 H  Et Cl 4-Br-phenylsulfonyloxy                                                                               wax                                          99 H  Et Cl 3-CF.sub.3 -phenylsulfonyloxy                                                                        oil                                         100 H  Et Cl 2-Br-phenylsulfonyloxy                                                                               oil                                         101 H  Et Cl 3-Cl-phenylsulfonyloxy                                                                               oil                                         102 H  Et Cl 4-Cl-2,5-diMe-phenylsulfonyloxy                                                                      oil                                         103 H  Et Cl 2-CF.sub.3 -phenylsulfonyloxy                                                                        wax                                         104 H  Et Cl 2,4-diF-phenylsulfonyloxy                                                                            oil                                         105 H  Et Cl 4-Pr-phenylsulfonyloxy                                                                               oil                                         106 H  Et Cl 4-Pr.sup.i -phenylsulfonyloxy                                                                        oil                                         107 H  Et Cl 2-Br-phenylsulfonyloxy                                                                               oil                                         108 H  Et Cl 2-naphthylsulfonyloxy oil                                         109 H  Et Cl 3-Cl-2-NO.sub.2 -phenylsulfonyloxy                                                                   oil                                         110 H  Et Cl 2-NO.sub.2 -4-CF.sub.3 -phenylsulfonyloxy                                                            141-3                                       111 H  Et Cl 3,5-diCl-phenylsulfonyloxy                                                                           oil                                         112 H  Et Cl 4-MeO-2,3,6-triMe-    oil                                                      phenylsulfonyloxy                                                 113 H  Et Cl 3-Me-phenylsulfonyloxy                                                                               oil                                         114 H  Et Cl 5-F-2-Me-phenylsulfonyloxy                                                                           oil                                         114 H  Et Cl penta-F-phenylsulfonyloxy                                                                            oil                                         115 H  Et Cl 2-F-phenylsulfonyloxy oil                                         116 H  Et Cl 4-Pr.sup.i -phenylsulfonyloxy                                                                        oil                                         117 H  Et Cl 2,4-diF-anilinocarbonyloxy                                                                           wax                                         118 H  Et Cl 3,5-di CF.sub.3 -phenylsulfonyloxy                                                                   oil                                         119 H  Et Cl                                                                                 ##STR17##            oil                                         120 H  Et Cl 3-Cl-2-Me-phenylsulfonyloxy                                                                          oil                                         121 H  Et Cl 2,3-diCl-phenylsulfonyloxy                                                                           oil                                         122 H  Et Cl 2,4,6-triCl-phenylsulfonyloxy                                                                        oil                                         123 H  Et Cl 4-(1,1-diMe-propyl)-  92-4                                                     phenylsulfonyloxy                                                 124 H  Et Cl 2-Cl-4-F-phenylsulfonyloxy                                                                           wax                                         125 H  Et Cl 4-Br-2,5-diF-phenylsulfonyloxy                                                                       wax                                         126 H  Et Cl 2,5-di-MeO-phenylsulfonyloxy                                                                         wax                                         127 H  Et Cl 3-Br-phenylsulfonyloxy                                                                               wax                                         128 H  Et Cl 2,6-di-Cl-phenylsulfonyloxy                                                                          oil                                         129 H  Et Cl 2-cyanophenylsulfonyloxy                                                                             oil                                         130 H  Et Cl 2,3,4-tri-Cl-phenylsulfonyloxy                                                                       97-9                                        131 H  Et Cl 4-biphenylylsulfonyloxy                                                                              oil                                         132 H  Et Cl 2-MeO-anilinocarbonyloxy                                                                             oil                                         133 H  Et Cl 2,4-di-MeO-anilinocarbonyloxy                                                                        149                                         135 H  Et Cl 3-F-anilinocarbonyloxy                                                                               wax                                         136 H  Et Cl N-cyclohexylcarbamoyloxy                                                                             118-22                                      137 H  Et Cl 2-NO.sub.2 -anilinocarbonyloxy                                                                       189                                         138 H  Et Cl 2-MeOCO-anilinocarbonyloxy                                                                           wax                                         139 H  Et Cl 4-MeS-anilinocarbonyloxy                                                                             148-52                                      140 H  Et Cl 2-Ph-anilinocarbonyloxy                                                                              196-204                                     141 H  Et Cl N-[1-(1-naphthyl)ethyl]-                                                                             wax                                                      carbamoyloxy                                                      142 H  Et Cl N-[3-(tri-EtO-Si)propyl]-                                                                            wax                                                      carbamoyloxy                                                      143 H  Et Cl 4-CF.sub.3 O-anilinocarbonyloxy                                                                      wax                                         144 H  Et Cl N-Bu-carbamoyloxy     90-1                                        145 H  Et Cl N-Pr.sup.i -carbamoyloxy                                                                             wax                                         146 H  Et Cl N-(2-chloroethyl)carbamoyloxy                                                                        oil                                         147 H  Et Cl 2-F-anilinocarbonyloxy                                                                               wax                                         148 H  Et Cl 2,3-diCl-anilinocarbonyloxy                                                                          wax                                         149 H  Et Cl 3-Cl-4-F-phenylsulfonyloxy                                                                           oil                                         150 H  Et Cl 4-Et-phenylsulfonyloxy                                                                               oil                                         151 H  Et Cl pivaloyloxy           oil                                         152 H  Et Cl benzoyloxy            123-6                                       153 H  Et Cl isobutyryloxy         61                                          154 H  Et Cl 2,4-diCl-benzoyloxy   wax                                         155 H  Et Cl 3-F-benzoyloxy        wax                                         156 H  Et Cl 2-furoyloxy           wax                                         157 H  Et Cl 2-Cl-benzoyloxy       wax                                         158 H  Et Cl --OCOCH(Me)Et         oil                                         159 H  Et Cl isovaleryloxy         oil                                         160 H  Et Cl cyclohexylcarbonyloxy oil                                         161 H  Et Cl 2-(MeOCO)-benzoyloxy  oil                                         162 H  Et Cl 3,4-diCl-benzoyloxy   wax                                         163 H  Et Cl 4-Cl-nicotinyloxy     oil                                         164 H  Et Cl cyclopentylcarbonyloxy                                                                               oil                                         165 H  Et Cl 2-phenylbutyryloxy    oil                                         166 H  Et Cl 4-F-benzoyloxy        wax                                         167 H  Et Cl valeryloxy            oil                                         168 H  Et Cl 2-thenoyloxy          wax                                         169 H  Et Cl propionyloxy          oil                                         170 H  Et Cl 3-Cl-benzoyloxy       oil                                         171 H  Et Cl 4-Cl-benzoyloxy       wax                                         172 H  Et Cl 2-Me-benzoyloxy       wax                                         173 H  Et Cl 2,3-diCl-benzoyloxy   wax                                         174 H  Et Cl 4-CF.sub.3 -benzoyloxy                                                                               oil                                         175 H  Et Cl 2-F-benzoyloxy        wax                                         176 H  Et Cl 2,6-diF-benzoyloxy    wax                                         177 H  Et Cl 4-Me-benzoyloxy       wax                                         178 H  Et Cl 2,4-diF-benzoyloxy    wax                                         179 H  Et Cl 2-MeO-benzoyloxy      oil                                         180 H  Et Cl 4-Br-benzoyloxy       wax                                         181 H  Et Cl 4-Bu.sup.t -benzoyloxy                                                                               oil                                         182 H  Et Cl 2-Cl-4-NO.sub.2 -benzoyloxy                                                                          oil                                         183 H  Et Cl 2-Cl-5-NO.sub.2 -benzoyloxy                                                                          wax                                         184 H  Et Cl 2-Cl-4-F-benzoyloxy   oil                                         185 H  Et Cl 3,5-diF-benzoyloxy    wax                                         186 H  Et Cl hexanoyloxy           oil                                         187 H  Et Cl cyclopropanylcarbonyloxy                                                                             oil                                         188 H  Et Cl methoxyacetyloxy      wax                                         189 H  Et Cl palmitoyloxy          wax                                         190 H  Et Cl 3-CF.sub.3 -benzoyloxy                                                                               oil                                         191 H  Et Cl butyryloxy            oil                                         192 H  Et Cl 2,5-diF-benzoyloxy    wax                                         193 H  Et Cl 1-naphthoyloxy        wax                                         194 H  Et Cl 2-naphthoyloxy        wax                                         195 H  Et Cl 4-I-benzoyloxy        oil                                         196 H  Et Cl cinnamoyloxy          solid                                       197 H  Et Cl methacryolyl          wax                                         __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR18##                                                                     Cmp                                                                               R.sup.9              Q R                       m.p./° C.             __________________________________________________________________________     500                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                                                      >200                                                   OC(═O)Ph                                         501                                                                               --OSO.sub.2 Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                                                      >200                                                   OC(═O)Ph                                         502                                                                               --OSO.sub.2 Me       I --CH.sub.2 OC(═O)Ph  98                          503                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   504                                                                               --OSO.sub.2 Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   505                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   506                                                                               --OSO.sub.2 Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   507                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         508                                                                               --OSO.sub.2 Me       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         509                                                                               --OSO.sub.2 CF.sub.3 I --CH.sub.2 O(C═O)Bu.sup.t                        510                                                                               --OSO.sub.2 Me       I --CH.sub.2 O(C═O)Bu.sup.t                        511                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               4-(propionyloxy)benzyl                               512                                                                               --OSO.sub.2 Me       Br                                                                               4-(propionyloxy)benzyl                               513                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               2-(ethoxycarbonyloxy)benzyl                          514                                                                               --OSO.sub.2 Me       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          515                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         516                                                                               --OSO.sub.2 Me       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         517                                                                               --OSO.sub.2 CF.sub.3 Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         518                                                                               --OSO.sub.2 Me       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         519                                                                               --OSO.sub.2 CF.sub.3 Br                                                                                ##STR19##                                           520                                                                               --OSO.sub.2 Me       Br                                                                                ##STR20##                                           521                                                                               --OSO.sub.2 -p-tolyl Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         522                                                                               --OSO.sub.2 -p-tolyl I --CH.sub.2 OC(═O)Ph                              523                                                                               --OSO.sub.2 -p-tolyl Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   524                                                                               --OSO.sub.2 -p-tolyl Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   525                                                                               --OSO.sub.2 -p-tolyl Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         526                                                                               --OSO.sub.2 -p-tolyl I --CH.sub.2 O(C═O)Bu.sup.t                        527                                                                               --OSO.sub.2 -p-tolyl Br                                                                               4-(propionyloxy)benzyl                               528                                                                               --OSO.sub.2 -p-tolyl Br                                                                               2-(ethoxycarbonyloxy)benzyl                          529                                                                               --OSO.sub.2 -p-tolyl Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         530                                                                               --OSO.sub.2 -p-tolyl Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         531                                                                               --OSO.sub.2 -p-tolyl Br                                                                                ##STR21##                                           532                                                                               OH                   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         533                                                                               OH                   I --CH.sub.2 OC(═O)Ph                              534                                                                               OH                   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   535                                                                               OH                   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   536                                                                               OH                   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         537                                                                               OH                   I --CH.sub.2 O(C═O)Bu.sup.t                        538                                                                               OH                   Br                                                                               4-(propionyloxy)benzyl                               539                                                                               OH                   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          540                                                                               OH                   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         541                                                                               OH                   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         542                                                                               OH                   Br                                                                                ##STR22##                                           543                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenyl)                OC(═O)Ph                                         544                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       I --CH.sub.2 OC(═O)Ph                                 phenyl)                                                                     545                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenyl)                OC(═O)Bu.sup.t                                   546                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenyl)                OC(═O)Pr.sup.i                                   547                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                       phenyl)                OC(═O)Ph                                         548                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                           phenyl)                                                                     549                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               4-(propionyloxy)benzyl                                  phenyl)                                                                     550                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                             phenyl)                                                                     551                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                       phenyl)                OC(═O)Ph                                         552                                                                               --OC(═O)CH.sub.2 -(4-PhO-                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                            phenyl)                                                                     553                                                                               --OC(═O)CH.sub.2 -(4-PhO-  phenyl)                                                              Br                                                                                ##STR23##                                           554                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         555                                                                               pyrrolidinecarbonyloxy                                                                              I --CH.sub.2 OC(═O)Ph                              556                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   557                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   558                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         559                                                                               pyrrolidinecarbonyloxy                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        560                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               4-(propionyloxy)benzyl                               561                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          562                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         563                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         564                                                                               pyrrolidinecarbonyloxy                                                                              Br                                                                                ##STR24##                                           565                                                                               --OC(═O)Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         566                                                                               --OC(═O)Me       I --CH.sub.2 OC(═O)Ph                              567                                                                               --OC(═O)Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   568                                                                               --OC(═O)Me       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   569                                                                               --OC(═O)Me       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         570                                                                               --OC(═O)Me       I --CH.sub.2 O(C═O)Bu.sup.t                        571                                                                               --OC(═O)Me       Br                                                                               4-(propionyloxy)benzyl                               572                                                                               --OC(═O)Me       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          573                                                                               --OC(═O)Me       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         574                                                                               --OC(═O)Me       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         575                                                                               --OC(═O)Me       Br                                                                                ##STR25##                                           576                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         577                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         I --CH.sub.2 OC(═O)Ph                              578                                                                               --OC(═O)NPr.sup.1.sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   579                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   580                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         581                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         I --CH.sub.2 O(C═O)Bu.sup.t                        582                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               4-(propionyloxy)benzyl                               583                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               2-(ethoxycarbonyloxy)benzyl                          584                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         585                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         586                                                                               --OC(═O)NPr.sup.i.sub.2                                                                         Br                                                                                ##STR26##                                           587                                                                               morpholinecarbonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         588                                                                               morpholinecarbonyloxy                                                                               I --CH.sub.2 OC(═O)Bu.sup.t                        589                                                                               morpholinecarbonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   590                                                                               morpholinecarbonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   591                                                                               morpholinecarbonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         592                                                                               morpholinecarbonyloxy                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        593                                                                               morpholinecarbonyloxy                                                                               Br                                                                               4-(propionyloxy)benzyl                               594                                                                               morpholinecarbonyloxy                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          595                                                                               morpholinecarbonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         596                                                                               morpholinecarbonyloxy                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         597                                                                               morpholinecarbonyloxy                                                                               Br                                                                                ##STR27##                                           598                                                                               phenacyloxy          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         599                                                                               phenacyloxy          I --CH.sub.2 OC(═O)Ph                              600                                                                               phenacyloxy          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(∇O)Bu.sup.t                              601                                                                               phenacyloxy          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   602                                                                               phenacyloxy          Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         603                                                                               phenacyloxy          I --CH.sub.2 O(C═O)Bu.sup.t                        604                                                                               phenacyloxy          Br                                                                               4-(propionyloxy)benzyl                               605                                                                               phenacyloxy          Br                                                                               2-(ethoxycarbonyloxy)benzyl                          606                                                                               phenacyloxy          Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         607                                                                               phenacyloxy          Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         608                                                                               phenacyloxy          Br                                                                                ##STR28##                                           609                                                                               --OC(═O)OEt      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         610                                                                               --OC(═O)OEt      I --CH.sub.2 OC(═O)Ph                              611                                                                               --OC(═O)OEt      Br                                                                               --CH.sub.2 C(═O)-phenylene-                                                OC(═O)Bu.sup.t                                   612                                                                               --OC(═O)OEt      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   613                                                                               --OC(═O)OEt      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         614                                                                               --OC(═O)OEt      I --CH.sub.2 O(C═O)Bu.sup.t                        615                                                                               --OC(═O)OEt      Br                                                                               4-(propionyloxy)benzyl                               616                                                                               --OC(═O)OEt      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          617                                                                               --OC(═O)OEt      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         618                                                                               --OC(═O)OEt      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         619                                                                               --OC(═O)OEt      Br                                                                                ##STR29##                                           620                                                                               --OC(═O)NHMe     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         621                                                                               --OC(═O)NHMe     I --CH.sub.2 OC(═O)Ph                              622                                                                               --OC(═O)NHMe     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   623                                                                               --OC(═O)NHMe     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   624                                                                               --OC(═O)NHMe     Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         625                                                                               --OC(═O)NHMe     I --CH.sub.2 O(C═O)Bu.sup.t                        626                                                                               --OC(═O)NHMe     Br                                                                               4-(propionyloxy)benzyl                               627                                                                               --OC(═O)NHMe     Br                                                                               2-(ethoxycarbonyloxy)benzyl                          628                                                                               --OC(═O)NHMe     Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         629                                                                               --OC(═O)NHMe     Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         630                                                                               --OC(═O)NHMe     Br                                                                                ##STR30##                                           631                                                                               --OC(═O)OMe      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         632                                                                               --OC(═O)OMe      I --CH.sub.2 OC(═O)Ph                              633                                                                               --OC(═O)OMe      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   634                                                                               --OC(═O)OMe      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   635                                                                               --OC(═O)OMe      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         636                                                                               --OC(═O)OMe      I --CH.sub.2 O(C═O)Bu.sup.t                        637                                                                               --OC(═O)OMe      Br                                                                               4-(propionyloxy)benzyl                               638                                                                               --OC(═O)OMe      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          639                                                                               --OC(═O)OMe      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         640                                                                               --OC(═O)OMe      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         641                                                                               --OC(═O)OMe      Br                                                                                ##STR31##                                           642                                                                               phenylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         643                                                                               phenylsulfonyloxy    I --CH.sub.2 OC(═O)Ph                              644                                                                               phenylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   645                                                                               phenylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   646                                                                               phenylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         647                                                                               phenylsulfonyloxy    I --CH.sub.2 O(C═O)Bu.sup.t                        648                                                                               phenylsulfonyloxy    Br                                                                               4-(propionyloxy)benzyl                               649                                                                               phenylsulfonyloxy    Br                                                                               2-(ethoxycarbonyloxy)benzyl                          650                                                                               phenylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         651                                                                               phenylsulfonyloxy    Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         652                                                                               phenylsulfonyloxy    Br                                                                                ##STR32##                                           653                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         654                                                                               4-F-phenylsulfonyloxy                                                                               I --CH.sub.2 OC(═O)Ph                              655                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   656                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   657                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         658                                                                               4-F-phenylsulfonyloxy                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        659                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               4-(propionyloxy)benzyl                               660                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          661                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         662                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         663                                                                               4-F-phenylsulfonyloxy                                                                               Br                                                                                ##STR33##                                           664                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         665                                                                               4-Cl-phenylsulfonyloxy                                                                              I --CH.sub.2 OC(═O)Ph                              666                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   667                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   668                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         669                                                                               4-Cl-phenylsulfonyloxy                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        670                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               4-(propionyloxy)benzyl                               671                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          672                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         673                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         674                                                                               4-Cl-phenylsulfonyloxy                                                                              Br                                                                                ##STR34##                                           675                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         676                                                                               2-Cl-phenylsulfonyloxy                                                                              I --CH.sub.2 OC(═O)Ph                              677                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   678                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   679                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         680                                                                               2-Cl-phenylsulfonyloxy                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        681                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               4-(propionyloxy)benzyl                               682                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          683                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         684                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         685                                                                               2-Cl-phenylsulfonyloxy                                                                              Br                                                                                ##STR35##                                           686                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         687                                                                               4-tBu-phenylsulfonyloxy                                                                             I --CH.sub.2 OC(═O)Ph                              688                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   689                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   690                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         691                                                                               4-tBu-phenylsulfonyloxy                                                                             I --CH.sub.2 O(C═O)Bu.sup.t                        692                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               4-(propionyloxy)benzyl                               693                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               2-(ethoxycarbonyloxy)benzyl                          694                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         695                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         696                                                                               4-tBu-phenylsulfonyloxy                                                                             Br                                                                                ##STR36##                                           697                                                                               ethylsufonyloxy      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         698                                                                               ethylsufonyloxy      I --CH.sub.2 OC(═O)Ph                              699                                                                               ethylsufonyloxy      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   700                                                                               ethylsufonyloxy      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   701                                                                               ethylsufonyloxy      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         702                                                                               ethylsufonyloxy      I --CH.sub.2 O(C═O)Bu.sup.t                        703                                                                               ethylsufonyloxy      Br                                                                               4-(propionyloxy)benzyl                               704                                                                               ethylsufonyloxy      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          705                                                                               ethylsufonyloxy      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         706                                                                               ethylsufonyloxy      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         707                                                                               ethylsufonyloxy      Br                                                                                ##STR37##                                           708                                                                               4-(acetamido)-       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsufonyloxy       OC(═O)Ph                                         709                                                                               4-(acetamido)-       I --CH.sub.2 OC(═O)Ph                                 phenylsufonyloxy                                                            710                                                                               4-(acetamido)-       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsufonyloxy       OC(═O)Bu.sup.t                                   711                                                                               4-(acetamido)-       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsufonyloxy       OC(═O)Pr.sup.i                                   712                                                                               4-(acetamido)-       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                       phenylsufonyloxy       OC(═O)Ph                                         713                                                                               4-(acetamido)-       I --CH.sub.2 O(C═O)Bu.sup.t                           phenylsufonyloxy                                                            714                                                                               4-(acetamido)-       Br                                                                               4-(propionyloxy)benzyl                                  phenylsufonyloxy                                                            715                                                                               4-(acetamido)-       Br                                                                               2-(ethoxycarbonyloxy)benzyl                             phenylsufonyloxy                                                            716                                                                               4-(acetamido)-       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                       phenylsufonyloxy       OC(═O)Ph                                         717                                                                               4-(acetamido)-       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                            phenylsufonyloxy                                                            718                                                                               4-(acetamido)-  phenylsufonyloxy                                                                    Br                                                                                ##STR38##                                           719                                                                               2,4-diCl-phenylsulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         720                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          I --CH.sub.2 OC(═O)Ph                              721                                                                               2,4-diCl-phenylsulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   722                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   723                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         724                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          I --CH.sub.2 O(C═O)Bu.sup.t                        725                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               4-(propionyloxy)benzyl                               726                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               2-(ethoxycarbonyloxy)benzyl                          727                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         728                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         729                                                                               2,4-CiCl-phenylsulfonyloxy                                                                          Br                                                                                ##STR39##                                           730                                                                               3,4-diMeO-           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         731                                                                               3,4-diMeO-           I --CH.sub.2 OC(═O)Ph                                 phenylsulfonyloxy                                                           732                                                                               3,4-diMeO-           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Bu.sup.t                                   733                                                                               3,4-diMeO-           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Pr.sup.i                                   734                                                                               3,4-diMeO-           Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         735                                                                               3,4-diMeO-           I --CH.sub.2 O(C═O)Bu.sup.t                           phenylsulfonyloxy                                                           736                                                                               3,4-diMeO-           Br                                                                               4-(propionyloxy)benzyl                                  phenylsulfonyloxy                                                           737                                                                               3,4-diMeO-           Br                                                                               2-(ethoxycarbonyloxy)benzyl                             phenylsulfonyloxy                                                           738                                                                               3,4-diMeO-           Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         739                                                                               3,4-diMeO-           Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                            phenylsulfonyloxy                                                           740                                                                               3,4-diMeO-  phenylsulfonyloxy                                                                       Br                                                                                ##STR40##                                           741                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         742                                                                               4-MeO-phenylsulfonyloxy                                                                             I --CH.sub.2 OC(═O)Ph                              743                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   744                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   745                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         746                                                                               4-MeO-phenylsulfonyloxy                                                                             I --CH.sub.2 O(C═O)Bu.sup.t                        747                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               4-(propionyloxy)benzyl                               748                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               2-(ethoxycarbonyloxy)benzyl                          749                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         750                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         751                                                                               4-MeO-phenylsulfonyloxy                                                                             Br                                                                                ##STR41##                                           752                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         753                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       I --CH.sub.2 OC(═O)Ph                              754                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   755                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   756                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         757                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                        758                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               4-(propionyloxy)benzyl                               759                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          760                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         761                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         762                                                                               2-CF.sub.3 -phenylsulfonyloxy                                                                       Br                                                                                ##STR42##                                           763                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         764                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         I --CH.sub.2 OC(═O)Ph                              765                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               --CH.sub.2 C(═O)-phenylene-                                                OC(═O)Bu.sup.t                                   766                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   767                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         768                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         I --CH.sub.2 O(C═O)Bu.sup.t                        769                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               4-(propionyloxy)benzyl                               770                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               2-(ethoxycarbonyloxy)benzyl                          771                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         772                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         773                                                                               3-Cl-4-Me-phenylsulfonyloxy                                                                         Br                                                                                ##STR43##                                           774                                                                               3-NO.sub.2 -4-Me-    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         775                                                                               3-NO.sub.2 -4-Me-    I --CH.sub.2 OC(═O)Ph                                 phenylsulfonyloxy                                                           776                                                                               3-NO.sub.2 -4-Me-    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Bu.sup.t                                   777                                                                               3-NO.sub.2 -4-Me-    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                       phenylsulfonyloxy      OC(═O)Pr.sup.i                                   778                                                                               3-NO.sub.2 -4-Me-    Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         779                                                                               3-NO.sub.2 -4-Me-    I --CH.sub.2 O(C═O)Bu.sup.t                           phenylsulfonyloxy                                                           780                                                                               3-NO.sub.2 -4-Me-    Br                                                                               4-(propionyloxy)benzyl                                  phenylsulfonyloxy                                                           781                                                                               3-NO.sub.2 -4-Me-    Br                                                                               2-(ethoxycarbonyloxy)benzyl                             phenylsulfonyloxy                                                           782                                                                               3-NO.sub.2 -4-Me-    Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                       phenylsulfonyloxy      OC(═O)Ph                                         783                                                                               3-NO.sub.2 -4-Me-    Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                            phenylsulfonyloxy                                                           784                                                                               3-NO.sub.2 -4-Me-  phenylsulfonyloxy                                                                Br                                                                                ##STR44##                                           785                                                                               propylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         786                                                                               propylsulfonyloxy    I --CH.sub.2 OC(═O)Ph                              787                                                                               propylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   788                                                                               propylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   789                                                                               propylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         790                                                                               propylsulfonyloxy    I --CH.sub.2 O(C═O)Bu.sup.t                        791                                                                               propylsulfonyloxy    Br                                                                               4-(propionyloxy)benzyl                               792                                                                               propylsulfonyloxy    Br                                                                               2-(ethoxycarbonyloxy)benzyl                          793                                                                               propylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         794                                                                               propylsulfonyloxy    Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         795                                                                               propylsulfonyloxy    Br                                                                                ##STR45##                                           796                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         797                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 OC(═O)Ph                              798                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   799                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   800                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         801                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                        802                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(propionyloxy)benzyl                               803                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          804                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         805                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         806                                                                               3-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                                ##STR46##                                           807                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         808                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 OC(═O)Ph                              809                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   810                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   811                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         812                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                        813                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(propionyloxy)benzyl                               814                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          815                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         816                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         817                                                                               4-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                                ##STR47##                                           818                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         819                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 OC(═O)Ph                              820                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O )-p-phenylene-                                             OC(═O)Bu.sup.t                                   821                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   822                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         823                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                        824                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(propionyloxy)benzyl                               825                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          826                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         827                                                                               2-NO.sub.2 -phenylsulfonyloxy                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         828                                                                               2-NO2-phenylsulfonyloxy                                                                             Br                                                                                ##STR48##                                           829                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         830                                                                               4-I-phenylsulfonyloxy                                                                               I --CH.sub.2 OC(═O)Ph                              831                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   832                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   833                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         834                                                                               4-I-phenylsulfonyloxy                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        835                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               4-(propionyloxy)benzyl                               836                                                                               4-1-phenylsulfonyloxy                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          837                                                                               4-I-phenylsulfonyloxy                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         838                                                                               4-l-phenylsulfonyloxy                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         839                                                                               4-l-phenylsulfonyloxy                                                                               Br                                                                                ##STR49##                                           840                                                                               isopropylsulfonyloxy Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         841                                                                               isopropylsulfonyloxy I --CH.sub.2 OC(═O)Ph                              842                                                                               isopropylsulfonyloxy Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   843                                                                               isopropylsulfonyloxy Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   844                                                                               isopropylsulfonyloxy Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         845                                                                               isopropylsulfonyloxy I --CH.sub.2 O(C═O)Bu.sup.t                        846                                                                               isopropylsulfonyloxy Br                                                                               4-(propionyloxy)benzyl                               847                                                                               isopropylsulfonyloxy Br                                                                               2-(ethoxycarbonyloxy)benzyl                          848                                                                               isopropylsulfonyloxy Br                                                                               --CH 2C(═O)-m-phenylene-                                                   OC(═O)Ph                                         849                                                                               isopropylsulfonyloxy Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         850                                                                               isopropylsulfonyloxy Br                                                                                ##STR50##                                           851                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         852                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      I --CH.sub.2 OC(═O)Ph                              853                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   854                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   855                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         856                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      I --CH.sub.2 O(C═O)Bu.sup.t                        857                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               4-(propionyloxy)benzyl                               858                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          859                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         860                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         861                                                                               2-CF.sub.3 O-phenylsulfonyloxy                                                                      Br                                                                                ##STR51##                                           862                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         863                                                                               OSO.sub.2 CCl.sub.3  I --CH.sub.2 OC(═O)Ph                              864                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   865                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   866                                                                               OSO.sub.2 CC.sub.3   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         867                                                                               OSO.sub.2 CCl.sub.3  I --CH.sub.2 O(C═O)Bu.sup.t                        868                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               4-(propionyloxy)benzyl                               869                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               2-(ethoxycarbonyloxy)benzyl                          870                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         871                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         872                                                                               OSO.sub.2 CCl.sub.3  Br                                                                                ##STR52##                                           873                                                                               OSO.sub.2 CCl.sub.3  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         874                                                                               OSO.sub.2 CCl.sub.2  I --CH.sub.2 OC(═O)Ph                              875                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   876                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   877                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         878                                                                               OSO.sub.2 CCl.sub.2  I --CH.sub.2 O(C═O)Bu.sup.t                        879                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               4-(propionyloxy)benzyl                               880                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               2-(ethoxycarbonyloxy)benzyl                          881                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         882                                                                               OSO.sub.2 CCl.sub.2  Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         883                                                                               OSO.sub.2 CCl.sub.3  Br                                                                                ##STR53##                                           884                                                                               butylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         885                                                                               butylsulfonyloxy     I --CH.sub.2 OC(═O)Ph                              886                                                                               butylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   887                                                                               butylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   888                                                                               butylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         889                                                                               butylsulfonyloxy     I --CH.sub.2 O(C═O)Bu.sup.t                        890                                                                               butylsulfonyloxy     Br                                                                               4-(propionyloxy)benzyl                               891                                                                               butylsulfonyloxy     Br                                                                               2-(ethoxycarbonyloxy)benzyl                          892                                                                               butylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         893                                                                               butylsulfonyloxy     Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         894                                                                               butylsulfonyloxy     Br                                                                                ##STR54##                                           895                                                                               benzylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         896                                                                               benzylsulfonyloxy    I --CH.sub.2 OC(═O)Ph                              897                                                                               benzylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   898                                                                               benzylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   899                                                                               benzylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         900                                                                               benzylsulfonyloxy    I --CH.sub.2 O(C═O)Bu.sup.t                        901                                                                               benzylsulfonyloxy    Br                                                                               4-(propionyloxy)benzyl                               902                                                                               benzylsulfonyloxy    Br                                                                               2-(ethoxycarbonyloxy)benzyl                          903                                                                               benzylsulfonyloxy    Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         904                                                                               benzylsulfonyloxy    Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         905                                                                               benzylsulfonyloxy    Br                                                                                ##STR55##                                           906                                                                               octylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         907                                                                               octylsulfonyloxy     I --CH.sub.2 OC(═O)Ph                              908                                                                               octylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   909                                                                               octylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   910                                                                               octylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         911                                                                               octylsulfonyloxy     I --CH.sub.2 O(C═O)Bu.sup.t                        912                                                                               octylsulfonyloxy     Br                                                                               4-(propionyloxy)benzyl                               913                                                                               octylsulfonyloxy     Br                                                                               2-(ethoxycarbonyloxy)benzyl                          914                                                                               octylsulfonyloxy     Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         915                                                                               octylsulfonyloxy     Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         916                                                                               octylsulfonyloxy     Br                                                                                ##STR56##                                           917                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         918                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       I --CH.sub.2 OC(═O)Ph                              919                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   920                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   921                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         922                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       I --CH.sub.2 O(C═O)Bu.sup.t                        923                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               4-(propionyloxy)benzyl                               924                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               2-(ethoxycarbonyloxy)benzyl                          925                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         926                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         927                                                                               2-NO.sub.2 -benzylsulfonyloxy                                                                       Br                                                                                ##STR57##                                           928                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         929                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          I --CH.sub.2 OC(═O)Ph                              930                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   931                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   932                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         933                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          I --CH.sub.2 O (C═O)Bu.sup.t                       934                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               4-(propionyloxy)benzyl                               935                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               2-(ethoxycarbonyloxy)benzyl                          936                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         937                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                               4-(CF.sub.3 O-benzyl)methyl                          938                                                                               5-Br-thienyl-2-sulfonyloxy                                                                          Br                                                                                ##STR58##                                           939                                                                                ##STR59##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-  OC(═O)Ph      940                                                                                ##STR60##           I --CH.sub.2 OC(═O)Ph                              941                                                                                ##STR61##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   942                                                                                ##STR62##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   943                                                                                ##STR63##           Br                                                                               --CH.sub.2 C(═O)-o-phenylene-  OC(═O)Ph      944                                                                                ##STR64##           I --CH.sub.2 O(C═O)Bu.sup.t                        945                                                                                ##STR65##           Br                                                                               4-(propionyloxy)benzyl                               946                                                                                ##STR66##           Br                                                                               2-(ethoxycarbonyloxy)benzyl                          947                                                                                ##STR67##           Br                                                                               --CH.sub.2 C(═O)-m-phenylene-  OC(═O)Ph      948                                                                                ##STR68##           Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         949                                                                                ##STR69##           Br                                                                                ##STR70##                                           950                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         951                                                                               --OSO.sub.2 NMe.sub.2                                                                               I --CH.sub.2 OC(═O)Ph                              952                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   953                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   954                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         955                                                                               --OSO.sub.2 NMe.sub.2                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        956                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               4-(propionyloxy)benzyl                               957                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          958                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         959                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         960                                                                               --OSO.sub.2 NMe.sub.2                                                                               Br                                                                                ##STR71##                                           961                                                                                ##STR72##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-  OC(═O)Ph      962                                                                                ##STR73##           I --CH.sub.2 OC(═O)Ph                              963                                                                                ##STR74##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   964                                                                                ##STR75##           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   965                                                                                ##STR76##           Br                                                                               --CH.sub.2 C(═O)-o-phenylene-  OC(═O)Ph      966                                                                                ##STR77##           I --CH.sub.2 O(C═O)Bu.sup.t                        967                                                                                ##STR78##           Br                                                                               4-(propionyloxy)benzyl                               968                                                                                ##STR79##           Br                                                                               2-(ethoxycarbonyloxy)benzyl                          969                                                                                ##STR80##           Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                    970                                                                                ##STR81##           Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         971                                                                                ##STR82##           Br                                                                                ##STR83##                                           972                                                                               --OP(O)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         973                                                                               --OP(O)Me.sub.2      I --CH.sub.2 OC(═O)Ph                              974                                                                               --OP(O)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   975                                                                               --OP(O)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   976                                                                               --OP(O)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         977                                                                               --OP(O)Me.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        978                                                                               --OP(O)Me.sub.2      Br                                                                               4-(propionyloxy)benzyl                               979                                                                               --OP(O)Me.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          980                                                                               --OP(O)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         981                                                                               --OP(O)Me.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         982                                                                               --OP(O)Me.sub.2      Br                                                                                ##STR84##                                           983                                                                               --OP(O)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         984                                                                               --OP(O)Et.sub.2      I --CH.sub.2 OC(═O)Ph                              985                                                                               --OP(O)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   986                                                                               --OP(O)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   987                                                                               --OP(O)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         988                                                                               --OP(O)Et.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        989                                                                               --OP(O)Et.sub.2      Br                                                                               4-(propionyloxy)benzyl                               990                                                                               --OP(O)Et.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          991                                                                               --OP(O)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         992                                                                               --OP(O)Et.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         993                                                                               --OP(O)Et.sub.2      Br                                                                                ##STR85##                                           994                                                                               --OP(O)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         995                                                                               --OP(O)Ph.sub.2      I --CH.sub.2 OC(═O)Ph                              996                                                                               --OP(O)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   997                                                                               --OP(O)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   998                                                                               --OP(O)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         999                                                                               --OP(O)Ph.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        1000                                                                              --OP(O)Ph.sub.2      Br                                                                               4-(propionyloxy)benzyl                               1001                                                                              --OP(O)Ph.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1002                                                                              --OP(O)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1003                                                                              --OP(O)Ph.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1004                                                                              --OP(O)Ph.sub.2      Br                                                                                ##STR86##                                           1005                                                                              --OP(O)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1006                                                                              --OP(O)(Me)Ph        I --CH.sub.2 OC(═O)Ph                              1007                                                                              --OP(O)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1008                                                                              --OP(O)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1009                                                                              --OP(O)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1010                                                                              --OP(O)(Me)Ph        I --CH.sub.2 O(C═O)Bu.sup.t                        1011                                                                              --OP(O)(Me)Ph        Br                                                                               4-(propionyloxy)benzyl                               1012                                                                              --OP(O)(Me)Ph        Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1013                                                                              --OP(O)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1014                                                                              --OP(O)(Me)Ph        Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1015                                                                              --OP(O)(Me)Ph        Br                                                                                ##STR87##                                           1016                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1017                                                                              --OP(O)(cyclohexyl).sub.2                                                                           I --CH.sub.2 OC(═O)Ph                              1018                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1019                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1020                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1021                                                                              --OP(O)(cyclohexyl).sub.2                                                                           I --CH.sub.2 O(C═O)Bu.sup.t                        1022                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               4-(propionyloxy)benzyl                               1023                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1024                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1025                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1026                                                                              --OP(O)(cyclohexyl).sub.2                                                                           Br                                                                                ##STR88##                                           1027                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1028                                                                              --OP(O)(methoxy).sub.2                                                                              I --CH.sub.2 OC(═O)Ph                              1029                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1030                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1031                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1032                                                                              --OP(O)(methoxy).sub.2                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        1033                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               4-(propionyloxy)benzyl                               1034                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1035                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1036                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1037                                                                              --OP(O)(methoxy).sub.2                                                                              Br                                                                                ##STR89##                                           1038                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1039                                                                              --OP(O)(ethoxy).sub.2                                                                               I --CH.sub.2 OC(═O)Ph                              1040                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1041                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1042                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1043                                                                              --OP(O)(ethoxy).sub.2                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        1044                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               4-(propionyloxy)benzyl                               1045                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1046                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1047                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1048                                                                              --OP(O)(ethoxy).sub.2                                                                               Br                                                                                ##STR90##                                           1049                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1050                                                                              --OP(O)(propoxy).sub.2                                                                              I --CH.sub.2 OC(═O)Ph                              1051                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1052                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1053                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1054                                                                              --OP(O)(propoxy).sub.2                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        1055                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               4-(propionyloxy)benzyl                               1056                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1057                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1058                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1059                                                                              --OP(O)(propoxy).sub.2                                                                              Br                                                                                ##STR91##                                           1060                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1061                                                                              --OP(O)(isopropoxy).sub.2                                                                           I --CH.sub.2 OC(═O)Ph                              1062                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1063                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1064                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1065                                                                              --OP(O)(isopropoxy).sub.2                                                                           I --CH.sub.2 O(C═O)Bu.sup.t                        1066                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               4-(propionyloxy)benzyl                               1067                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1068                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1069                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1070                                                                              --OP(O)(isopropoxy).sub.2                                                                           Br                                                                                ##STR92##                                           1071                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1072                                                                              --OP(O)(butoxy).sub.2                                                                               I --CH.sub.2 OC(═O)Ph                              1073                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1074                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1075                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1076                                                                              --OP(O)(butoxy).sub.2                                                                               I --CH.sub.2 O(C═O)Bu.sup.t                        1077                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               4-(propionyloxy)benzyl                               1078                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1079                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1080                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1081                                                                              --OP(O)(butoxy).sub.2                                                                               Br                                                                                ##STR93##                                           1082                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1083                                                                              --OP(O)(pentoxy).sub.2                                                                              I --CH.sub.2 OC(═O)Ph                              1084                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1085                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1086                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1087                                                                              --OP(O)(pentoxy).sub.2                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        1088                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               4-(propionyloxy)benzyl                               1089                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1090                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1091                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1092                                                                              --OP(O)(pentoxy).sub.2                                                                              Br                                                                                ##STR94##                                           1093                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1094                                                                              --OP(O)(phenoxy).sub.2                                                                              I --CH.sub.2 OC(═O)Ph                              1095                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1096                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1097                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1098                                                                              --OP(O)(phenoxy).sub.2                                                                              I --CH.sub.2 O(C═O)Bu.sup.t                        1099                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               4-(propionyloxy)benzyl                               1100                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1101                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1102                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1103                                                                              --OP(O)(phenoxy).sub.2                                                                              Br                                                                                ##STR95##                                           1104                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1105                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         I --CH.sub.2 OC(═O)Ph                              1106                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1107                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1108                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1109                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         I --CH.sub.2 O(C═O)Bu.sup.t                        1110                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               4-(propionyloxy)benzyl                               1111                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1112                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1113                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1114                                                                              --OP(O)(4-Cl-phenoxy).sub.2                                                                         Br                                                                                ##STR96##                                           1115                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1116                                                                              --OP(O)(4-toloxy).sub.2                                                                             I --CH.sub.2 OC(═O)Ph                              1117                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1118                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1119                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1120                                                                              --OP(O)(4-toloxy).sub.2                                                                             I --CH.sub.2 O(C═O)Bu.sup.t                        1121                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               4-(propionyloxy)benzyl                               1122                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1123                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1124                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1125                                                                              --OP(O)(4-toloxy).sub.2                                                                             Br                                                                                ##STR97##                                           1126                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1127                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            I --CH.sub.2 OC(═O)Ph                              1128                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1129                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1130                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1131                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            I --CH.sub.2 O(C═O)Bu.sup.t                        1132                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               4-(propionyloxy)benzyl                               1133                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1134                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1135                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1136                                                                              --OP(O)(NMe.sub.2).sub.2                                                                            Br                                                                                ##STR98##                                           1137                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1138                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            I --CH.sub.2 OC(═O)Ph                              1139                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1140                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1141                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1142                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            I --CH.sub.2 O(C═O)Bu.sup.t                        1143                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               4-(propionyloxy)benzyl                               1144                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1145                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1146                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1147                                                                              --OP(O)(NEt.sub.2).sub.2                                                                            Br                                                                                ##STR99##                                           1148                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1149                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      I --CH.sub.2 OC(═O)Ph                              1150                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1151                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1152                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1153                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      I --CH.sub.2 O(C═O)Bu.sup.t                        1154                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               4-(propionyloxy)benzyl                               1155                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1156                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1157                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1158                                                                              --OP(O)(NPr.sup.i.sub.2).sub.2                                                                      Br                                                                                ##STR100##                                          1159                                                                              --OP(O)(NHPh).sub.2  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1160                                                                              --OP(O)(NHPh).sub.2  I --CH.sub.2 OC(═O)Ph                              1161                                                                              --OP(O)(NHPh).sub.2  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1162                                                                              --OP(O)(NHPh).sub.2  Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1163                                                                              --OP(O)(NHPh).sub.2  Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1164                                                                              --OP(O)(NHPh).sub.2  I --CH.sub.2 O(C═O)Bu.sup.t                        1165                                                                              --OP(O)(NHPh).sub.2  Br                                                                               4-(propionyloxy)benzyl                               1166                                                                              --OP(O)(NHPh).sub.2  Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1167                                                                              --OP(O)(NHPh).sub.2  Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1168                                                                              --OP(O)(NHPh).sub.2  Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1169                                                                              --OP(O)(NHPh).sub.2  Br                                                                                ##STR101##                                          1170                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1171                                                                              --OP(O)(NHPh)(OPh)   I --CH.sub.2 OC(═O)Ph                              1172                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1173                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1174                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1175                                                                              --OP(O)(NHPh)(OPh)   I --CH.sub.2 O(C═O)Bu.sup.t                        1176                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               4-(propionyloxy)benzyl                               1177                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1178                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1179                                                                              --OP(O)(NHPh)(OPh)   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1180                                                                              --OP(O)(NHPh)(OPh)   Br                                                                                ##STR102##                                          1181                                                                              --OP(S)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1182                                                                              --OP(S)Me.sub.2      I --CH.sub.2 OC(═O)Ph                              1183                                                                              --OP(S)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1184                                                                              --OP(S)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1185                                                                              --OP(S)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1186                                                                              --OP(S)Me.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        1187                                                                              --OP(S)Me.sub.2      Br                                                                               4-(propionyloxy)benzyl                               1188                                                                              --OP(S)Me.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1189                                                                              --OP(S)Me.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1190                                                                              --OP(S)Me.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1191                                                                              --OP(S)Me.sub.2      Br                                                                                ##STR103##                                          1192                                                                              --OP(S)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1193                                                                              --OP(S)Et.sub.2      I --CH.sub.2 OC(═O)Ph                              1194                                                                              --OP(S)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1195                                                                              --OP(S)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1196                                                                              --OP(S)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1197                                                                              --OP(S)Et.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        1198                                                                              --OP(S)Et.sub.2      Br                                                                               4-(propionyloxy)benzyl                               1199                                                                              --OP(S)Et.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1200                                                                              --OP(S)Et.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1201                                                                              --OP(S)Et.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1202                                                                              --OP(S)Et.sub.2      Br                                                                                ##STR104##                                          1203                                                                              --OP(S)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1204                                                                              --OP(S)Ph.sub.2      I --CH.sub.2 OC(═O)Ph                              1205                                                                              --OP(S)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1206                                                                              --OP(S)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1207                                                                              --OP(S)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1208                                                                              --OP(S)Ph.sub.2      I --CH.sub.2 O(C═O)Bu.sup.t                        1209                                                                              --OP(S)Ph.sub.2      Br                                                                               4-(propionyloxy)benzyl                               1210                                                                              --OP(S)Ph.sub.2      Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1211                                                                              --OP(S)Ph.sub.2      Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1212                                                                              --OP(S)Ph.sub.2      Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1213                                                                              --OP(S)Ph.sub.2      Br                                                                                ##STR105##                                          1214                                                                              --OP(S)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1215                                                                              --OP(S)(Me)Ph        I --CH.sub.2 OC(═O)Ph                              1216                                                                              --OP(S)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1217                                                                              --OP(S)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1218                                                                              --OP(S)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1219                                                                              --OP(S)(Me)Ph        I --CH.sub.2 O(C═O)Bu.sup.t                        1220                                                                              --OP(S)(Me)Ph        Br                                                                               4-(propionyloxy)benzyl                               1221                                                                              --OP(S)(Me)Ph        Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1222                                                                              --OP(S)(Me)Ph        Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1223                                                                              --OP(S)(Me)Ph        Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1224                                                                              --OP(S)(Me)Ph        Br                                                                                ##STR106##                                          1225                                                                              --OP(S)(OMe).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC═O)Ph                                          1226                                                                              --OP(S)(OMe).sub.2   I --CH.sub.2 OC(═O)Ph                              1227                                                                              --OP(S)(OMe).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1228                                                                              --OP(S)(OMe).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1229                                                                              --OP(S)(OMe).sub.2   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1230                                                                              --OP(S)(OMe).sub.2   I --CH.sub.2 O(C═O)Bu.sup.t                        1231                                                                              --OP(S)(OMe).sub.2   Br                                                                               4-(propionyloxy)benzyl                               1232                                                                              --OP(S)(OMe).sub.2   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1233                                                                              --OP(S)(OMe).sub.2   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1234                                                                              --OP(S)(OMe).sub.2   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1235                                                                              --OP(S)(OMe).sub.2   Br                                                                                ##STR107##                                          1236                                                                              --OP(S)(OEt).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1237                                                                              --OP(S)(OEt).sub.2   I --CH.sub.2 OC(═O)Ph                              1238                                                                              --OP(S)(OEt).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1239                                                                              --OP(S)(OEt).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1240                                                                              --OP(S)(OEt).sub.2   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1241                                                                              --OP(S)(OEt).sub.2   I --CH.sub.2 O(C═O)Bu.sup.t                        1242                                                                              --OP(S)(OEt).sub.2   Br                                                                               4-(propionyloxy)benzyl                               1243                                                                              --OP(S)(OEt).sub.2   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1244                                                                              --OP(S)(OEt).sub.2   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1245                                                                              --OP(S)(OEt).sub.2   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1246                                                                              --OP(S)(OEt).sub.2   Br                                                                                ##STR108##                                          1247                                                                              --OP(S)(OPr).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1248                                                                              --OP(S)(OPr).sub.2   I --CH.sub.2 OC(═O)Ph                              1249                                                                              --OP(S)(OPr).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1250                                                                              --OP(S)(OPr).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1251                                                                              --OP(S)(OPr).sub.2   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1252                                                                              --OP(S)(OPr).sub.2   I --CH.sub.2 O(C═O)Bu.sup.t                        1253                                                                              --OP(S)(OPr).sub.2   Br                                                                               4-(propionyloxy)benzyl                               1254                                                                              --OP(S)(OPr).sub.2   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1255                                                                              --OP(S)(OPr).sub.2   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1256                                                                              --OP(S)(OPr).sub.2   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1257                                                                              --OP(S)(OPr).sub.2   Br                                                                                ##STR109##                                          1258                                                                              --OP(S)(OBu).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1259                                                                              --OP(S)(OBu).sub.2   I --CH.sub.2 OC(═O)Ph                              1260                                                                              --OP(S)(OBu).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1261                                                                              --OP(S)(OBu).sub.2   Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1262                                                                              --OP(S)(OBu).sub.2   Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1263                                                                              --OP(S)(OBu).sub.2   I --CH.sub.2 O(C═O)Bu.sup.t                        1264                                                                              --OP(S)(OBu).sub.2   Br                                                                               4-(propionyloxy)benzyl                               1265                                                                              --OP(S)(OBu).sub.2   Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1266                                                                              --OP(S)(OBu).sub.2   Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1267                                                                              --OP(S)(OBu).sub.2   Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1268                                                                              --OP(S)(OBu).sub.2   Br                                                                                ##STR110##                                          1269                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                         1270                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            I --CH.sub.2 OC(═O)Ph                              1271                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Bu.sup.t                                   1272                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Pr.sup.i                                   1273                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                         1274                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            I --CH.sub.2 O(C═O)Bu.sup.t                        1275                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               4-(propionyloxy)benzyl                               1276                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               2-(ethoxycarbonyloxy)benzyl                          1277                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               --CH.sub.2 C(═O)-m-phenylene-                                              OC(═O)Ph                                         1278                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                               4-(CF.sub.3 O-benzoyl)methyl                         1279                                                                              --OP(S)(NMe.sub.2).sub.2                                                                            Br                                                                                ##STR111##                                          __________________________________________________________________________

                  TABLE 5                                                          ______________________________________                                          ##STR112##                                                                    Cmp       R.sup.9      position  m.p./° C.                              ______________________________________                                         2000      --OSO.sub.2 Me                                                                              2                                                       2001      --OSO.sub.2 CF.sub.3                                                                        2                                                       2002      --OSO.sub.2 CF.sub.3                                                                        3                                                       2003      --OSO.sub.2 Me                                                                              3                                                       ______________________________________                                    

                                      TABLE 6                                      __________________________________________________________________________      ##STR113##                                                                    Cmp R.sup.9                                                                               position                                                                            Q  R                       m.p./° C.                    __________________________________________________________________________     3000                                                                               --OSO.sub.2 Me                                                                        2    Br --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                                3001                                                                               --OSO.sub.2 Me                                                                        3    Br --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                                3002                                                                               --OSO.sub.2 CF.sub.3                                                                  2    Br --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                                3003                                                                               --OSO.sub.2 CF.sub.3                                                                  3    Br --CH.sub.2 C(═O)-p-phenylene-                                              OC(═O)Ph                                                3004                                                                               --OSO.sub.2 Me                                                                        2    I  --CH.sub.2 OC(═O)Ph                                     3005                                                                               --OSO.sub.2 Me                                                                        3    I  --CH.sub.2 OC(═O)Ph                                     3006                                                                               --OSO.sub.2 CF.sub.3                                                                  2    I  --CH.sub.2 OC(═O)Ph                                     3007                                                                               --OSO.sub.2 CF.sub.3                                                                  3    I  --CH.sub.2 OC(═O)Ph                                     3008                                                                               --OSO.sub.2 Me                                                                        2    Br --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                                3009                                                                               --OSO.sub.2 Me                                                                        3    Br --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                                3010                                                                               --OSO.sub.2 CF.sub.3                                                                  2    Br --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                                3011                                                                               --OSO.sub.2 CF.sub.3                                                                  3    Br --CH.sub.2 C(═O)-o-phenylene-                                              OC(═O)Ph                                                3012                                                                               --OSO.sub.2 Me                                                                        2    Br 4-CF.sub.3 O-phenacyl                                       3013                                                                               --OSO.sub.2 Me                                                                        3    Br 4-CF.sub.3 O-phenacyl                                       3014                                                                               --OSO.sub.2 CF.sub.3                                                                  2    Br 4-CF.sub.3 O-phenacyl                                       3015                                                                               --OSO.sub.2 CF.sub.3                                                                  3    Br 4-CF.sub.3 O-phenacyl                                       3016                                                                               --OSO.sub.2 Me                                                                        2    Br                                                                                 ##STR114##                                                 3017                                                                               --OSO.sub.2 Me                                                                        3    Br                                                                                 ##STR115##                                                 3018                                                                               --OSO.sub.2 CF.sub.3                                                                  2    Br                                                                                 ##STR116##                                                 3019                                                                               --OSO.sub.2 CF.sub.3                                                                  3    Br                                                                                 ##STR117##                                                 3020                                                                               --OSO.sub.2 Me                                                                        2    Br 2-(ethoxycarbonyloxy)benzyl                                 3021                                                                               --OSO.sub.2 Me                                                                        3    Br 2-(ethoxycarbonyloxy)benzyl                                 3022                                                                               --OSO.sub.2 CF.sub.3                                                                  2    Br 2-(ethoxycarbonyloxy)benzyl                                 3023                                                                               --OSO.sub.2 CF.sub.3                                                                  3    Br 2-(ethoxycarbonyloxy)benzyl                                 __________________________________________________________________________

C. BIOLOGICAL EXAMPLES

Use as Insecticide/Acaricide

Example 1

Cut stems of bean plants (Phaseolus vulgaris) carrying one leaf are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 spider mites (Tetranychus urticae). The plant leaf and the spider mites are sprayed to run-off point with an aqueous solution or dispersion of the formulated preparation to be examined. After run off, plants and mites are stored in a controlled environment chamber (16 hours of light/day, 25° C., 40-60% relative humidity). After 6 days storage, the effect of the preparation on all stages of the spider mites is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 1-3 12, 13, 17, 18, 21, 24-27, 29-37, 43, 44, 47, 48, 49, 50, 52, 91-98, 100-114, 116-139, 142, 144-149, 151-154, 156-161, 163-165, 169, 171, 174, 176, 178, 179, 18, 182, 184, 187, 191-197, 501 and 502 cause a mortality of 90-100%.

In a similar test, using a full population of spider mites on the leaves, compounds 4-6 and 9-11 cause a mortality of 90-100%.

Example 2

Germinated field bean seeds (Vicia fabae) with radicles are transferred into brown bottles filled with tap water and subsequently populated with approximately 100 black bean aphids (Aphis fabae). Plants and aphids are sprayed to run-off point with an aqueous dispersion or solution of the formulated preparation to be examined. After the solution has run off, plants and animals are stored in a controlled environment chamber (16 hours of light/day, 25° C., 40-60% relative humidity). After 3 days storage, the effect of the preparation on the aphids is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 2, 17, 18, 19, 21, 26-32, 34-36, 46, 48, 49, 97, 105, 113, 132, 134, 135, 137, 139, 144-147, 151-154, 158-161, 182, 184, 186-188, 191, 192, 500 and 501 cause a 90-100% mortality of the aphids.

In a similar test, using a heavy infestation of aphids, after 3 days compounds 4, 6-8, 10 and 11 cause a mortality of 90-100%.

Example 3

The leaves of 12 rice plants having a stem length of 8 cm are dipped for 5 seconds into an aqueous solution or dispersion of the formulated preparation to be examined. After the solution has run off, the rice plants treated in this manner are placed in a Petri dish and populated with about 20 larvae (L3 stage) of the rice leafhopper species (Nilaparvata lugens). The Petri dish is sealed and then stored in a controlled environment chamber (16 hours of light/day, 25° C., 40-60% relative humidity). After 6 days storage, the mortality of the leafhopper larvae is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 2, 3, 13, 17, 25-27, 29, 30, 33-36, 42, 46, 49, 50, 93, 97-99, 102-107, 110, 113, 126, 132-134, 136, 137, 139, 144-149, 151, 153, 182, 184, 185, 187, 188, 197 and 500-502 cause a mortality of 90-100%.

In a similar test, using only 10 larvae, maintained in a growing receptacle at 21° C., after 4 days compounds 6, 8 and 10 cause a mortality of 90-100%.

Example 4

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Pieces of filter paper with about 30, 24-hour-old eggs of the tobacco budworm (Heliothis virescens) are dipped into an aqueous solution or dispersion of the formulated preparation to be examined for about 5 seconds and subsequently placed into the Petri dish. A further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then kept at about 25° C., in a controlled environment chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 2, 3, 13, 17, 26, 28-31, 46, 145-146 197, and 500-502 cause a mortality of 90-100%.

Example 5

A Petri dish whose bottom is covered with filter paper and which contains about 5 ml of culture medium is prepared. Ten L2 larvae of the Egyptian cotton leaf worm (Spodoptera littoralis) are counted into a small beaker. 200 μl of an aqueous solution or dispersion of the formulated preparation to be examined are pipetted into the beaker. The treated larvae are then poured into the Petri dish and a further 200 μl of the aqueous solution are spread over the culture medium. The Petri dish is sealed and then stored at about 25° C. in a controlled environment chamber. After 6 days storage, the effect of the preparation on the larvae is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 2, 3, 13, 17, 29-31, 42, 93, 104, 132, 133 and 145 cause a mortality of 90-100%.

In a similar test, using 10 L4 larvae, maintained at c. 23° C., after 4 days, compound 6 causes a mortality of 90-100%.

Example 6

A Petri dish, half of whose bottom is covered with filter paper and contains a germinated maize corn on a moist cotton pad, is prepared. About 50, 4-5-day-old eggs of the southern corn rootworm (Diabrotica undecimpunctata) are transferred onto the filter paper. Three drops of 200 μl of an aqueous solution or dispersion of the formulated preparation to be examined are pipetted onto the eggs, and the rest is pipetted onto the maize corn. The Petri dish is sealed and then stored at about 25° C. in a controlled environment chamber chamber. After 6 days storage, the effect of the preparation on the eggs and the larvae which may have hatched from these is determined. At a concentration of 300 ppm (based on the content of active compound), compounds 2, 3, 17, 29, 31, 126, 132, 133, 135-137, 145 and 502 cause a mortality of 90-100%.

In a similar test, using 10 L2 larvae, maintained in a growing receptacle at 26° C., after 2 days, compound 6, 8 10 and 11 cause a mortality of 90-100%.

Example 7

Part A of the test (contact activity): Approximately 5000 recently hatched, active (mobile) larvae (2nd development stage) of the root gall nematode (Meloidogyne incognita) are placed into a glass vessel containing an aqueous solution or dispersion of the formulated preparation to be examined (final volume 20 ml). After the nematode larvae have been continually exposed for 6 days, the percentage of the specimen which has ceased to move (been immobilised) owing to the effect of the preparation is determined by comparison with the untreated controls (percent nematicidal contact activity).

Part B of the test (soil-drench activity): For this test, the entire solution or dispersion from part A of the test (active compound and pre-treated nematode larvae) is poured into a pot filled with 60 ml of soil in which three 9-day-old cucumber plants (Cucumis sativus) have been planted. This drench application reduces the active compound content, based on the volume of the soil, to one third of the active compound content in part A of the test. After two weeks in a greenhouse at about 26° C. (the plants being watered twice a day), the root balls of the cucumber plants are carefully washed out from the soil mixture infested with nematodes. The number of root galls per plant is counted and compared with the infestation of untreated control plants. The reduction of infestation in percent as activity criterion is calculated using Abbott's formula (percent nematicidal soil-drench activity).

At a concentration of 3 ppm in part A of the test and 1 ppm in part B of the test, respectively, (based in each case on the content of active compound), compounds 2, 3, 17, 30, 31, 46, 117, 126, 132, 133, 135, 143, 144, 146, 500 and 502 have a 90-100% activity against the root gall nematode Meloidogyne incognita. In addition, compounds 3, 30, 46, 500 and 502 are active in the part A test.

Fungicide Tests

Compounds are assessed for activity against one or more of the following:

Plasmopara viticola: vine downy mildew

Erysiphe graminis f. sp. tritici: wheat powdery mildew

Pyricularia oryzae: rice blast

Leptosphaeria nodorum: glume blotch

Pellicularia sasakii: rice sheath blight

Phytophthora infestans: late tomato or potato blight

Aqueous solutions or dispersions of the compounds at the desired concentration, including a wetting agent, were applied by spray or by drenching the stem base of the test plants, as appropriate. Plants or plant parts were then inoculated with appropriate test pathogens and kept under controlled environment conditions suitable for maintaining plant growth and development of the disease. After an appropriate time, the degree of infection of the affected part of the plant was visually estimated. Compounds are assessed on a score of 1 to 3 where 1 is little or no control, 2 is moderate control and 3 is good to total control. At a concentration of 500 ppm (w/v) or less, the following compounds scored 2 or more against the fungi specified

Plasmopara viticola

17, 18, 23, 31, 32

Erysiphe graminis f. sp. tritici

17, 18, 30, 31, 500, 501

Pyricularia oryzae

5, 21, 28, 30, 32

Leptosphaeria nodorum

3, 17, 18

Pellicularia sasakii

17

Phytophthora infestans

3, 23, 28, 30, 31, 32 

What is claimed is:
 1. A compound of formula I, N-oxides or salts ##STR118## in which q is 0, 1 or 2R¹ is hydrogen, halogen, (C₁ -C₈)-alkyl, (C₁ -C₈)-haloalkyl, (C₁ -C₈)-alkoxy or (C₃ -C₆)-cycloalkyl; R² and R³ are identical or different and are each hydrogen, (C₁ -C₈)-alkyl, (C₂ -C₈)-alkenyl, (C₂ -C₈)-alkynyl, (C₁ -C₈)-alkoxy, halogen, hydroxy, cyano, nitro, thiocyanato, (C₁ -C₈)-alkoxycarbonyl, (C₁ -C₈)-alkylthio, (C₁ -C₈)-alkylsulfinyl, (C₁ -C₈)-alkylsulfonyl, amino, (C₁ -C₈)-alkylamino, (C₁ -C₈)-dialkylamino or (C₃ -C₆)-cycloalkyl, and in which in the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkynyl, alkanoyl, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino or dialkylamino, groups, a saturated carbon unit can be replaced by oxygen, S(O)_(x), where x=0, 1 or 2 or by dimethylsilyl and further in these groups up to 3 hydrogen atoms can be replaced by halogen and in the case of fluorine also all hydrogen atoms can be replaced by fluorine; or R² and R³ together with the carbon atoms to which they are attached form an unsaturated 5- or 6-membered carbocyclic ring which may, if it is a 5-membered ring, contain an oxygen or sulfur atom instead of CH₂, or which may, if it is a 6-membered ring, contain one or two nitrogen atoms instead of one or two CH units, and which may be substituted by 1, 2 or 3 identical or different radicals, these radicals being (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, halogen, (C₁ -C₄)-alkoxy or (C₁ -C₄)-haloalkoxy; or R² and R³ together with the carbon atoms to which they are attached form a saturated 5-, 6- or 7-membered carbocyclic ring which may contain oxygen and/or sulfur instead of one or two CH₂ groups and which may be substituted by 1, 2 or 3 (C₁ -C₄)-alkyl groups; A is CH and D is N⁺ R×1/n Q^(n-) or A is N and D is N⁺ R×1/n Q^(n-) or A is CH or N and D is N or A is N⁺ R×1/n Q^(n-) and D is N, R is CR⁶ R⁷ D^(a) R⁸, Q^(n-) is an inorganic or organic anion, n being 1, 2, 3 or 4; X is NH, O or S(O)_(q), (q is 0, 1 or 2); R⁴ and R^(4'), which may be the same or different, are hydrogen, halogen, (C₁ -C₄)-alkyl, (C₁ -C₄)-halogenalkyl, (C₁ -C₄)-alkoxy or (C₁ -C₄)-alkylthio; R⁵ is the group ##STR119## l is 1, 2, 3, 4 or 5; m is 0, 1, 2, 3 or 4, each R⁹, which may be the same or different from any other R⁹, is (C₂ -C₈)-haloalkenyloxy, (C₂ -C₈)-haloalkynyl, (C₂ -C₈)-haloalkynyloxy, (C₁ -C₄)-haloalkoxy-(C₁ -C₄)-haloalkoxy, oxiran-2-ylmethoxy, oxetan-2-ylmethoxy, isopropylidenoamino-oxy, isopropylidenamino-oxy-(C₁ -C₄)-alkoxy, formyl, --SF₅, hydroxy or heterocyclyloxy, in which the last named group may be substituted by up to three of the same or different D¹ R¹², cyano, nitro or halogen, or R⁹ is a group Z--R¹¹, in which Z is OSO₂, NR¹³ SO₂, UC(═W)V, U¹ P(W¹)(V¹ R¹¹)V², SO₂ NR¹³, SO₂ O, NR¹³ SO₂ NR¹³, OSO₂ NR¹³, NR¹³ SO₂ O, Si(OR)¹³ R¹³, N(O)R¹³, NR¹³ O, NR¹³ NR¹³, N═N, N═, NR¹³ --N═, D¹⁻⁻ N═ and U¹ is a direct bond, oxygen, NR¹³ or sulfur, U is oxygen, NR¹³ or sulfur, or when W or V is NR¹³ or sulfur, it can also be a direct bond, W is oxygen, NR¹³⁰ or sulfur, and R¹³⁰ is hydrogen, nitro, cyano, optionally substituted alkyl, optionally substituted acyloxy, optionally substituted aryl, optionally substituted heteroaryl, hydroxy, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, mono- or disubstituted amino; W¹ is oxygen or sulfur, V, V¹, V², independently of each other are a direct bond, NR¹³, oxygen or sulfur, each R¹³, which may be the same or different from any other R¹³, is hydroxy, alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyl or optionally substituted acyloxy, R¹¹ is (C₁ -C₂₀)-alkyl, (C₂ -C₂₀)-alkenyl, (C₂ -C₂₀)-alkynyl, (C₃ -C₈)-cycloalkyl or (C₄ -C₈)-cycloalkenyl, in which groups optionally one or more, generally up to three, CH₂ -groups can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO₂, NR¹³ or SiR¹⁶ R¹⁷, and these groups may be substituted by up to three of the same or different D² R¹⁴, cyano, nitro or halogen, or R¹¹ is hydrogen, aryl or heterocyclyl, in which the last named group may be substituted by up to three of the same or different D³ R¹⁵, cyano, nitro or halogen, or when V is NR¹³, R¹³ and R¹¹ can together form a 4- to 8-membered ring, in which one or two CH₂ -groups, is replaced by oxygen; S(O)_(t), where t=0, 1 or 2, or NR¹⁹, in which D¹, D² and D³, independently of each other, are a direct bond, oxygen, S(O)_(k), SO₂ O, OSO₂, CO, OCO, COO, NR^(13'), SO₂ --NR^(13'), NR^(13') SO₂, ONR^(13'), NR^(13') O, NR^(13') CO, CONR^(13') or SiR¹⁶ R¹⁷, and k=0, 1 or 2 and R^(13') has the same meaning as R¹³, R¹⁶, R¹⁷, independently of each other, are (C₁ -C₄)-alkyl; R¹², R¹⁴ and R¹⁵ are hydrogen, C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl, C₂ -C₈ -alkynyl, C₃ -C₈ -cycloalkyl, C₄ -C₈ -cycloalkenyl, C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl, C₄ -C₈ -cycloalkenyl-C₁ -C₄ -alkyl, aryl, heterocyclyl, aryl-C₁ -C₄ -alkyl or heterocyclyl-C₁ -C₄ -alkyl, in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, CH₂ -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more of the same or different groups selected from halogen, hydroxy and cyano and in the case of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more of the same or different substituents R¹⁸ ; R¹⁸ is (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-haloalkoxy, cyano, nitro or halogen; R¹⁹ is hydrogen, (C₁ -C₈)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylthio, (C₃ -C₅)-cycloalkyl, (C₂ -C₄)-alkenyl, (C₂ -C₄)-alkynyl, (C₁ -C₄)-alkanoyl, (C₂ -C₄)-haloalkanoyl, (C₂ -C₄)-alkoxyalkyl, phenyl-(C₁ -C₄)-alkyl or phenyl and the phenyl groups are unsubstituted or substituted by one or more of the same or different substituents R²⁰, R²⁰ is (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, (C₁ -C₄)-alkoxy, (C₁ -C₄)-alkylthio, halogen or cyano; R¹⁰ is cyano, nitro, halogen, C₁ -C₈ -alkyl, C₂ -C₈ -alkenyl, C₂ -C₈ -alkynyl, C₃ -C₈ -cycloalkyl, C₄ -C₈ -cycloalkenyl, C₃ -C₈ -cycloalkyl-C₁ -C₄ -alkyl, C₄ -C₈ -cycloalkenyl-C₁ -C₄ -alkyl, aryl, heterocyclyl, aryl-C₁ -C₄ -alkyl or heterocyclyl-C₁ -C₄ -alkyl in which in any alkyl-, alkenyl- and alkynyl based groups optionally one or more, CH₂ -group can be replaced by hetero atom units O or S, the alkyl, alkenyl- and alkynyl groups, with or without the named varations, can also be optionally substituted by one or more of the same or different groups selected from halogen, hydroxy and cyano and in the case of of the last named 8 groups, the cycloaliphatic, aromatic or heterocyclic rings are unsubstituted or substituted by one or more of the same or different substituents R²¹, R²¹ has the same meaning as R¹⁸, or two adjacent R⁹ and/or R¹⁰ groups together with the carbon atoms two which they are attached can form an unsaturated 5- or 6-membered carbocyclic ring, which in a 5 membered ring, a CH₂ can be replaced by an oxygen- or sulfur atom and in a 6 membered ring, one or two CH units can be replaced by one or two nitrogen atoms or substituted by 1, 2 or 3 of the same or different groups selected from (C₁ -C₄)-alkyl, (C₁ -C₄)-haloalkyl, halogen, (C₁ -C₄)-alkoxy or (C₁ -C₄)-haloalkoxy; or two adjacent R⁹ and/or R¹⁰ groups together with the carbon atoms to which they are attached can form a saturated 5- or 6- or 7 membered carbocyclic ring, in which, one or two CH₂ units can be replaced by one or two oxygen and/or sulfur and can be substituted by 1, 2 or 3 (C₁ -C₄)-alkyl groups, and further whenA is CH and D is N⁺ R×1/n Q^(n-) or A is N and D is N⁺ R×1/n Q or A is N⁺ R×1/n Q^(n-) and D is N R⁹ can also be (C₂ -C₆)-alkynyl, (C₂ -C₆)-alkynyloxy or (C₂ -C₆)-haloalkenyl; R⁶ is hydrogen, halogen or C₁ -C₄ -alkyl or a negative charge, which can represent Q^(n-) R⁷ is hydrogen, halogen, CN, nitro, (C₁ -C₄)-alkoxycarbonyl, (C₁ -C₄)-alkylcarbamoyl, di-(C₁ -C₄)-alkylcarbamoyl, (C₁ -C₈)-alkoxy, (C₁ -C₈)-alkyl, (C₂ -C₈)-alkenyl, (C₂ -C₈)-alkynyl, aryl or (C₃ -C₈)-cycloalkyl. D^(a) is a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SO₂, C(═W^(a)), OC(═W^(a)), U^(a) (C═W^(a))V^(a) where U^(a) and V^(a) are a direct bond, NR⁷⁰, S or O, except V^(a) is not a bond when U^(a) is bond or O; SiR⁷² R⁷³, U^(b) (P═W^(b))V^(b) V^(c), U^(b) (SO₂)U^(c) where one of U^(b) and U^(c) is a direct bond, NR⁷⁰, S or O and the other is NR⁷⁰ ; U^(a) (CW^(a))(CW^(a))V^(b), NR⁷⁰ O, O NR⁷⁰, NR⁷⁰ NR⁷⁰, N═N, --N═, --NR⁷⁰ --N═ or --O--N═, and W^(a) is O, S or NR⁷¹ ; W^(b) is O or S; U^(a), V^(b) and V^(c), independently of each other are a direct bond, NR⁷⁰, S or O each R⁷⁰, which may be the same or different from any other R⁷⁰, is hydrogen, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino, optionally substituted acyloxy, and may also form a 4 to 8 membered with R⁶, R¹¹² OR R¹¹³, respectively with the D^(a), D¹² OR D¹³ to which they are attached; each R⁷¹, which may be the same or different from any other R⁷¹, is hydrogen, nitro, cyano, hydroxy, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heteroaryloxy, mono- or disubstituted amino or optionally substituted acyloxy; R⁷² and R⁷³ are alkyl or optionally substituted aryl; and R⁸ is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to three CH₂ units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO₂, NR⁷⁰ or Si R⁷² R⁷³ and can also be substituted by nitro, halogen, SF₅ or D¹² R¹¹², and in the case D^(a) is U^(b) P(═W^(b))V^(b) V^(c), the two R⁶ groups together with the V^(b) PV^(c), to which they are attached can form a 4 to 8 membered ring, D¹² is a direct bond, NR⁷⁰, N(O)R⁷⁰, O, S, SO, SiR⁷² R⁷³, U'(CW')V', U^(1') (PW^(1'))V^(1') V^(2'), U^(2') (SO₂)U^(3'), Si(OR⁷²)R⁷³, Si(OR⁷²)(OR⁷³), NR⁷⁰ O, ONR⁷⁰, NR⁷⁰ NR⁷⁰, N═N, ═N--, ═N--NR70-- ═N--O--, --N═, --NR⁷⁰ --N═ or --O--N═ and U', U^(1') V', V^(1') and V^(2'), independently of each other are a direct bond, NR⁷⁰, S or O W' is O, S or NR⁷¹ ; W^(1') is O or S; U^(2') and U^(3'), independently of each other are a direct bond, NR⁷⁰ or O; R¹¹² is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, in which up to CH₂ units in a carbon containing group can be replaced by carbonyl-, thiocarbonyl or O, S, SO, SO₂, NR⁷⁰ or SiR⁷² R⁷³ and can also be substituted by nitro, halogen, SF₅ or D¹³ R¹¹³ and in which two adjacent D¹² R¹¹² together with the carbons to which they are attached can form a condensed ring comprising 4 to 6 ring atoms which can be substituted one or more halogen or C₁ -C₄ -alkyl; is a negative charge for D¹² ═(CO)O, (SO₂)O, U^(1') (PW^(1'))V^(1') O which replaces the ion Q^(n-) ; or R¹¹² is hydrogen when D¹² is O(CO)NH, NR⁷⁰ (CO)NH, O(CS)NH, NR⁷⁰ (CS)NH, (CO)NH, (CS)NH, O(CO), NR⁷⁰ (CO), SO2NH; D¹³ has the same meaning as D¹² and R¹¹³ has the same meaning as R¹¹².
 2. A pesticidal composition comprising an effective amount of at least one compound as claimed in claim 1 together with the additives or auxiliaries which are customary for these applications.
 3. A method of controlling pests, which comprises applying an effective amount of a compound as claimed in claim 1 to the pest or its locus. 